EP2912022A1 - Substituted triazoles as herbicides - Google Patents
Substituted triazoles as herbicidesInfo
- Publication number
- EP2912022A1 EP2912022A1 EP13786569.7A EP13786569A EP2912022A1 EP 2912022 A1 EP2912022 A1 EP 2912022A1 EP 13786569 A EP13786569 A EP 13786569A EP 2912022 A1 EP2912022 A1 EP 2912022A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- alkyl
- phenyl
- haloalkyl
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004009 herbicide Substances 0.000 title claims description 39
- 150000003852 triazoles Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 680
- 239000000203 mixture Substances 0.000 claims abstract description 139
- 238000000034 method Methods 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 313
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- -1 4-fluoro-2-pyridinyl Chemical group 0.000 claims description 88
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 125000001188 haloalkyl group Chemical group 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 47
- 239000007787 solid Substances 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 230000002363 herbicidal effect Effects 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 24
- 239000004094 surface-active agent Substances 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 11
- 230000012010 growth Effects 0.000 claims description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 9
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- PKTJKKARCIJTJR-UHFFFAOYSA-N 2,2-difluoro-1,3-dioxolane Chemical group FC1(F)OCCO1 PKTJKKARCIJTJR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- URSWVMYVZUYSQF-UHFFFAOYSA-N 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine Chemical compound COC1=NN(C=2C=CC(=CC=2)C(F)(F)F)N=C1CC1=CC=NC(C(F)(F)F)=C1 URSWVMYVZUYSQF-UHFFFAOYSA-N 0.000 claims 2
- YKZQQUNPKGGXLN-UHFFFAOYSA-N 4-[[5-ethoxy-2-[4-(trifluoromethyl)phenyl]triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine Chemical compound CCOC1=NN(C=2C=CC(=CC=2)C(F)(F)F)N=C1CC1=CC=NC(C(F)(F)F)=C1 YKZQQUNPKGGXLN-UHFFFAOYSA-N 0.000 claims 1
- KQNXFONNTJRNPU-UHFFFAOYSA-N 4-[[5-methyl-2-[4-(trifluoromethyl)phenyl]triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine Chemical compound CC1=NN(C=2C=CC(=CC=2)C(F)(F)F)N=C1CC1=CC=NC(C(F)(F)F)=C1 KQNXFONNTJRNPU-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
- 241000192043 Echinochloa Species 0.000 description 94
- 240000008042 Zea mays Species 0.000 description 70
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 68
- 240000001592 Amaranthus caudatus Species 0.000 description 65
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 65
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 65
- 235000014716 Eleusine indica Nutrition 0.000 description 65
- 240000006122 Chenopodium album Species 0.000 description 64
- 235000009344 Chenopodium album Nutrition 0.000 description 64
- 241000209140 Triticum Species 0.000 description 64
- 235000021307 Triticum Nutrition 0.000 description 64
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 64
- 235000005822 corn Nutrition 0.000 description 64
- 240000006995 Abutilon theophrasti Species 0.000 description 63
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 63
- 241000196324 Embryophyta Species 0.000 description 63
- 244000025670 Eleusine indica Species 0.000 description 62
- 235000004135 Amaranthus viridis Nutrition 0.000 description 61
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 61
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 61
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 61
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 61
- 235000005476 Digitaria cruciata Nutrition 0.000 description 61
- 235000006830 Digitaria didactyla Nutrition 0.000 description 61
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 61
- 240000001549 Ipomoea eriocarpa Species 0.000 description 61
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 61
- 235000003403 Limnocharis flava Nutrition 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 60
- 238000002360 preparation method Methods 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 54
- 239000002904 solvent Substances 0.000 description 51
- 230000002829 reductive effect Effects 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000003112 inhibitor Substances 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- 240000007594 Oryza sativa Species 0.000 description 39
- 235000007164 Oryza sativa Nutrition 0.000 description 39
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- 235000009566 rice Nutrition 0.000 description 37
- 241000169130 Heteranthera limosa Species 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
- 241001290610 Abildgaardia Species 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 33
- 238000010992 reflux Methods 0.000 description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000009472 formulation Methods 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 23
- 238000012360 testing method Methods 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 125000000623 heterocyclic group Chemical group 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 15
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 12
- IEKZRNDXAHEKKI-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-5-methyltriazol-4-yl]oxy-2-(trifluoromethyl)pyridine Chemical compound CC1=NN(C=2C=CC(F)=CC=2)N=C1OC1=CC=NC(C(F)(F)F)=C1 IEKZRNDXAHEKKI-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 9
- 239000007800 oxidant agent Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
- 244000068988 Glycine max Species 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 8
- 235000007340 Hordeum vulgare Nutrition 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 7
- 229930192334 Auxin Natural products 0.000 description 7
- 239000005562 Glyphosate Substances 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 239000002363 auxin Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- 150000003871 sulfonates Chemical class 0.000 description 7
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 6
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 description 6
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 6
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 6
- 108010018763 Biotin carboxylase Proteins 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229940125758 compound 15 Drugs 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 108010001545 phytoene dehydrogenase Proteins 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 5
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 5
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 description 5
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 description 5
- 244000052363 Cynodon dactylon Species 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 240000005702 Galium aparine Species 0.000 description 5
- 235000014820 Galium aparine Nutrition 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 description 5
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 description 5
- 240000006694 Stellaria media Species 0.000 description 5
- 244000067505 Xanthium strumarium Species 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 229940126142 compound 16 Drugs 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 102000005396 glutamine synthetase Human genes 0.000 description 5
- 108020002326 glutamine synthetase Proteins 0.000 description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
- 229940097068 glyphosate Drugs 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 150000004669 very long chain fatty acids Chemical class 0.000 description 5
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 4
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 4
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 4
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 4
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- VDLCFICVTZPDKP-UHFFFAOYSA-N 4-[[5-ethoxy-2-(4-fluorophenyl)triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine Chemical compound CCOC1=NN(C=2C=CC(F)=CC=2)N=C1CC1=CC=NC(C(F)(F)F)=C1 VDLCFICVTZPDKP-UHFFFAOYSA-N 0.000 description 4
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 4
- 108010000700 Acetolactate synthase Proteins 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 0.000 description 4
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000005489 Bromoxynil Substances 0.000 description 4
- 241000209202 Bromus secalinus Species 0.000 description 4
- 235000005853 Cyperus esculentus Nutrition 0.000 description 4
- 244000152970 Digitaria sanguinalis Species 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 239000005510 Diuron Substances 0.000 description 4
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 description 4
- 239000005529 Florasulam Substances 0.000 description 4
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 description 4
- 239000005533 Fluometuron Substances 0.000 description 4
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 description 4
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 description 4
- 239000005578 Mesotrione Substances 0.000 description 4
- 239000005586 Nicosulfuron Substances 0.000 description 4
- FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 description 4
- 108010060806 Photosystem II Protein Complex Proteins 0.000 description 4
- 239000005597 Pinoxaden Substances 0.000 description 4
- 239000005606 Pyridate Substances 0.000 description 4
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 4
- 241001355178 Setaria faberi Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- 239000005620 Tembotrione Substances 0.000 description 4
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 4
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 4
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 4
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 description 4
- 230000008166 cellulose biosynthesis Effects 0.000 description 4
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 4
- BXIGJZDQFDFASM-UHFFFAOYSA-N cyclopyrimorate Chemical compound N=1N=C(Cl)C=C(OC(=O)N2CCOCC2)C=1OC=1C(C)=CC=CC=1C1CC1 BXIGJZDQFDFASM-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 description 4
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 4
- 150000002314 glycerols Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 4
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 4
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 235000001508 sulfur Nutrition 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- VIXCLRUCUMWJFF-KGLIPLIRSA-N (1R,5S)-benzobicyclon Chemical compound CS(=O)(=O)c1ccc(C(=O)C2=C(Sc3ccccc3)[C@H]3CC[C@H](C3)C2=O)c(Cl)c1 VIXCLRUCUMWJFF-KGLIPLIRSA-N 0.000 description 3
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1r,5s)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 3
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 description 3
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- DHYXNIKICPUXJI-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-(2,4-difluorophenyl)-5-oxo-n-propan-2-yl-1,2,4-triazole-4-carboxamide Chemical compound C=1C=C(F)C=C(F)C=1N(C(C)C)C(=O)N(C1=O)C=NN1C1=CC=C(Cl)C=C1Cl DHYXNIKICPUXJI-UHFFFAOYSA-N 0.000 description 3
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 3
- UUHXXNQVWVFJLW-UHFFFAOYSA-N 1-dimethoxyphosphorylethyl 2-(2,4-dichlorophenoxy)acetate Chemical compound COP(=O)(OC)C(C)OC(=O)COC1=CC=C(Cl)C=C1Cl UUHXXNQVWVFJLW-UHFFFAOYSA-N 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 3
- CZRVDACSCJKRFL-UHFFFAOYSA-N 2,5-dimethyl-4-[2-methylsulfonyl-4-(trifluoromethyl)benzoyl]-1h-pyrazol-3-one Chemical compound N1N(C)C(=O)C(C(=O)C=2C(=CC(=CC=2)C(F)(F)F)S(C)(=O)=O)=C1C CZRVDACSCJKRFL-UHFFFAOYSA-N 0.000 description 3
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 description 3
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 3
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 3
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 3
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 description 3
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 3
- KPSTXQYTZBZXMM-UHFFFAOYSA-N 2-[8-chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carbonyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2C(CCCC2=O)=O)=NC2=C(Cl)C=CC=C21 KPSTXQYTZBZXMM-UHFFFAOYSA-N 0.000 description 3
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 3
- UFAPVJDEYHLLBG-UHFFFAOYSA-N 2-{2-chloro-4-(methylsulfonyl)-3-[(tetrahydrofuran-2-ylmethoxy)methyl]benzoyl}cyclohexane-1,3-dione Chemical compound ClC1=C(COCC2OCCC2)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O UFAPVJDEYHLLBG-UHFFFAOYSA-N 0.000 description 3
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 description 3
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 3
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 3
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 3
- 239000002890 Aclonifen Substances 0.000 description 3
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 3
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 3
- 239000003666 Amidosulfuron Substances 0.000 description 3
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 3
- 239000005468 Aminopyralid Substances 0.000 description 3
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 description 3
- 241001666377 Apera Species 0.000 description 3
- 239000005469 Azimsulfuron Substances 0.000 description 3
- 239000005472 Bensulfuron methyl Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000005484 Bifenox Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000005492 Carfentrazone-ethyl Substances 0.000 description 3
- 239000005494 Chlorotoluron Substances 0.000 description 3
- 239000005496 Chlorsulfuron Substances 0.000 description 3
- 239000005497 Clethodim Substances 0.000 description 3
- 239000005500 Clopyralid Substances 0.000 description 3
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 description 3
- 239000005501 Cycloxydim Substances 0.000 description 3
- 244000108484 Cyperus difformis Species 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 description 3
- 239000005644 Dazomet Substances 0.000 description 3
- 239000005503 Desmedipham Substances 0.000 description 3
- 239000005504 Dicamba Substances 0.000 description 3
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 3
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 3
- 239000005507 Diflufenican Substances 0.000 description 3
- 239000005508 Dimethachlor Substances 0.000 description 3
- IKYICRRUVNIHPP-UHFFFAOYSA-N Dimethametryn Chemical compound CCNC1=NC(NC(C)C(C)C)=NC(SC)=N1 IKYICRRUVNIHPP-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 3
- 239000005514 Flazasulfuron Substances 0.000 description 3
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 3
- 239000005531 Flufenacet Substances 0.000 description 3
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 3
- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 description 3
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 description 3
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 3
- 239000005558 Fluroxypyr Substances 0.000 description 3
- 239000005559 Flurtamone Substances 0.000 description 3
- 239000005560 Foramsulfuron Substances 0.000 description 3
- 241001101998 Galium Species 0.000 description 3
- 239000005561 Glufosinate Substances 0.000 description 3
- 239000005563 Halauxifen-methyl Substances 0.000 description 3
- 239000005564 Halosulfuron methyl Substances 0.000 description 3
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 description 3
- 241000208818 Helianthus Species 0.000 description 3
- 239000005566 Imazamox Substances 0.000 description 3
- 239000005981 Imazaquin Substances 0.000 description 3
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 3
- 239000005567 Imazosulfuron Substances 0.000 description 3
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 description 3
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005570 Isoxaben Substances 0.000 description 3
- 239000005571 Isoxaflutole Substances 0.000 description 3
- 241000520028 Lamium Species 0.000 description 3
- 239000005572 Lenacil Substances 0.000 description 3
- 239000005573 Linuron Substances 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 3
- 239000005574 MCPA Substances 0.000 description 3
- 239000005575 MCPB Substances 0.000 description 3
- 101150039283 MCPB gene Proteins 0.000 description 3
- 239000002169 Metam Substances 0.000 description 3
- 239000005580 Metazachlor Substances 0.000 description 3
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 3
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 description 3
- 239000005582 Metosulam Substances 0.000 description 3
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 3
- 239000005583 Metribuzin Substances 0.000 description 3
- 239000005584 Metsulfuron-methyl Substances 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 3
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 3
- 239000005585 Napropamide Substances 0.000 description 3
- 239000005588 Oxadiazon Substances 0.000 description 3
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 3
- 239000005589 Oxasulfuron Substances 0.000 description 3
- 239000005590 Oxyfluorfen Substances 0.000 description 3
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 239000005643 Pelargonic acid Substances 0.000 description 3
- 239000005592 Penoxsulam Substances 0.000 description 3
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 description 3
- 241000745991 Phalaris Species 0.000 description 3
- 235000005632 Phalaris canariensis Nutrition 0.000 description 3
- 239000005594 Phenmedipham Substances 0.000 description 3
- 108010081996 Photosystem I Protein Complex Proteins 0.000 description 3
- 239000005595 Picloram Substances 0.000 description 3
- 239000005596 Picolinafen Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 3
- 239000005599 Profoxydim Substances 0.000 description 3
- 239000005600 Propaquizafop Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000005604 Prosulfuron Substances 0.000 description 3
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 3
- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 description 3
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 description 3
- RRKHIAYNPVQKEF-UHFFFAOYSA-N Pyriftalid Chemical compound COC1=CC(OC)=NC(SC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 RRKHIAYNPVQKEF-UHFFFAOYSA-N 0.000 description 3
- 239000005607 Pyroxsulam Substances 0.000 description 3
- 239000005616 Rimsulfuron Substances 0.000 description 3
- 239000005617 S-Metolachlor Substances 0.000 description 3
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 3
- 239000005618 Sulcotrione Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000005619 Sulfosulfuron Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 description 3
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical compound C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 3
- NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 description 3
- 239000005622 Thiencarbazone Substances 0.000 description 3
- 239000005624 Tralkoxydim Substances 0.000 description 3
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 3
- 239000005627 Triclopyr Substances 0.000 description 3
- 239000005629 Tritosulfuron Substances 0.000 description 3
- 241000972221 Urochloa decumbens Species 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 description 3
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 3
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- KWAIHLIXESXTJL-UHFFFAOYSA-N aminocyclopyrachlor Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 KWAIHLIXESXTJL-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 235000003484 annual ragweed Nutrition 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 3
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 3
- JEDYYFXHPAIBGR-UHFFFAOYSA-N butafenacil Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(Cl)C(C(=O)OC(C)(C)C(=O)OCC=C)=C1 JEDYYFXHPAIBGR-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- SILSDTWXNBZOGF-KUZBFYBWSA-N chembl111058 Chemical compound CCSC(C)CC1CC(O)=C(\C(CC)=N\OC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-KUZBFYBWSA-N 0.000 description 3
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 3
- 210000003763 chloroplast Anatomy 0.000 description 3
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 3
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 3
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 description 3
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 3
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 3
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 235000003488 common ragweed Nutrition 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 3
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 3
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 3
- ACDZDIIWZVQMIX-UHFFFAOYSA-N fenoxasulfone Chemical compound C1=C(Cl)C(OCC)=CC(Cl)=C1CS(=O)(=O)C1=NOC(C)(C)C1 ACDZDIIWZVQMIX-UHFFFAOYSA-N 0.000 description 3
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 3
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 3
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 3
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 3
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 3
- 150000003278 haem Chemical class 0.000 description 3
- KKLBEFSLWYDQFI-UHFFFAOYSA-N halauxifen Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C(O)=O)=C1F KKLBEFSLWYDQFI-UHFFFAOYSA-N 0.000 description 3
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 description 3
- 150000002390 heteroarenes Chemical class 0.000 description 3
- YFONKFDEZLYQDH-BOURZNODSA-N indaziflam Chemical compound CC(F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-BOURZNODSA-N 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 3
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 3
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 3
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 3
- 229940088649 isoxaflutole Drugs 0.000 description 3
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 3
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 3
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 3
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 3
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 3
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 description 3
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 3
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 3
- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 3
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 3
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 3
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 3
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 3
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 3
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 3
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 3
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 3
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 3
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 3
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 3
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 3
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 3
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 3
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 3
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 3
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 3
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 3
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 3
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 2
- ROBSGBGTWRRYSK-SNVBAGLBSA-N (2r)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C#N)C=C1F ROBSGBGTWRRYSK-SNVBAGLBSA-N 0.000 description 2
- NYHLMHAKWBUZDY-QMMMGPOBSA-N (2s)-2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl]oxypropanoic acid Chemical compound C1=C(Cl)C(C(=O)O[C@@H](C)C(O)=O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NYHLMHAKWBUZDY-QMMMGPOBSA-N 0.000 description 2
- LNGRZPZKVUBWQV-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LNGRZPZKVUBWQV-UHFFFAOYSA-N 0.000 description 2
- WMMQJAQJAPXWDO-UHFFFAOYSA-N (4-chlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(Cl)C=C1 WMMQJAQJAPXWDO-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- ADDQHLREJDZPMT-AWEZNQCLSA-N (S)-metamifop Chemical compound O=C([C@@H](OC=1C=CC(OC=2OC3=CC(Cl)=CC=C3N=2)=CC=1)C)N(C)C1=CC=CC=C1F ADDQHLREJDZPMT-AWEZNQCLSA-N 0.000 description 2
- PYKLUAIDKVVEOS-RAXLEYEMSA-N (e)-n-(cyanomethoxy)benzenecarboximidoyl cyanide Chemical compound N#CCO\N=C(\C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-RAXLEYEMSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 description 2
- PYCINWWWERDNKE-UHFFFAOYSA-N 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound N12N=C(CCC)C=CC2=NC(Cl)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 PYCINWWWERDNKE-UHFFFAOYSA-N 0.000 description 2
- IXWKBUKANTXHJH-UHFFFAOYSA-N 1-[5-chloro-2-methyl-4-(5-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl)pyrazol-3-yl]sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C=2OC(C)CON=2)C)=N1 IXWKBUKANTXHJH-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 description 2
- 239000002794 2,4-DB Substances 0.000 description 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 2
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 2
- QEGVVEOAVNHRAA-UHFFFAOYSA-N 2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)sulfanylbenzoic acid Chemical compound COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C(O)=O)=N1 QEGVVEOAVNHRAA-UHFFFAOYSA-N 0.000 description 2
- KZNDFYDURHAESM-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl KZNDFYDURHAESM-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FEZZUSJWVCRXRG-UHFFFAOYSA-N 4-methyl-1-oxido-2-[4-(trifluoromethyl)phenyl]triazol-1-ium Chemical compound N1=C(C)C=[N+]([O-])N1C1=CC=C(C(F)(F)F)C=C1 FEZZUSJWVCRXRG-UHFFFAOYSA-N 0.000 description 2
- AZQAWSUKRHRXEI-UHFFFAOYSA-N 5-ethoxy-2-(4-fluorophenyl)-n-methoxy-n-methyltriazole-4-carboxamide Chemical compound N1=C(C(=O)N(C)OC)C(OCC)=NN1C1=CC=C(F)C=C1 AZQAWSUKRHRXEI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 239000005470 Beflubutamid Substances 0.000 description 2
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 2
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 2
- 239000005476 Bentazone Substances 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- XTFNPKDYCLFGPV-OMCISZLKSA-N Bromofenoxim Chemical compound C1=C(Br)C(O)=C(Br)C=C1\C=N\OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XTFNPKDYCLFGPV-OMCISZLKSA-N 0.000 description 2
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 description 2
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 2
- NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 2
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 2
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 239000005499 Clomazone Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 239000005502 Cyhalofop-butyl Substances 0.000 description 2
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- HCRWJJJUKUVORR-UHFFFAOYSA-N Desmetryn Chemical compound CNC1=NC(NC(C)C)=NC(SC)=N1 HCRWJJJUKUVORR-UHFFFAOYSA-N 0.000 description 2
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 2
- DHWRNDJOGMTCPB-UHFFFAOYSA-N Dimefuron Chemical compound ClC1=CC(NC(=O)N(C)C)=CC=C1N1C(=O)OC(C(C)(C)C)=N1 DHWRNDJOGMTCPB-UHFFFAOYSA-N 0.000 description 2
- 239000005509 Dimethenamid-P Substances 0.000 description 2
- QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 description 2
- 239000005630 Diquat Substances 0.000 description 2
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 2
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000044408 Eriochloa Species 0.000 description 2
- 241001299722 Eriochloa villosa Species 0.000 description 2
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 description 2
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 description 2
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 description 2
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 description 2
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 2
- FICWGWVVIRLNRB-UHFFFAOYSA-N Flucetosulfuron Chemical compound COCC(=O)OC(C(C)F)C1=NC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 FICWGWVVIRLNRB-UHFFFAOYSA-N 0.000 description 2
- AOQMRUTZEYVDIL-UHFFFAOYSA-N Flupoxam Chemical compound C=1C=C(Cl)C(COCC(F)(F)C(F)(F)F)=CC=1N1N=C(C(=O)N)N=C1C1=CC=CC=C1 AOQMRUTZEYVDIL-UHFFFAOYSA-N 0.000 description 2
- 239000005535 Flurochloridone Substances 0.000 description 2
- UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JLLJHQLUZAKJFH-UHFFFAOYSA-N Isouron Chemical compound CN(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 JLLJHQLUZAKJFH-UHFFFAOYSA-N 0.000 description 2
- 241000110847 Kochia Species 0.000 description 2
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 2
- 244000303225 Lamium amplexicaule Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 2
- 239000005579 Metamitron Substances 0.000 description 2
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 2
- 239000005581 Metobromuron Substances 0.000 description 2
- WLFDQEVORAMCIM-UHFFFAOYSA-N Metobromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C=C1 WLFDQEVORAMCIM-UHFFFAOYSA-N 0.000 description 2
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 2
- 240000005561 Musa balbisiana Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FFQPZWRNXKPNPX-UHFFFAOYSA-N N-benzyl-2-[4-fluoro-3-(trifluoromethyl)phenoxy]butanamide Chemical compound C=1C=CC=CC=1CNC(=O)C(CC)OC1=CC=C(F)C(C(F)(F)F)=C1 FFQPZWRNXKPNPX-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- NTBVTCXMRYKRTB-UHFFFAOYSA-N N-{2-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-6-(methoxymethyl)phenyl}-1,1-difluoromethanesulfonamide Chemical compound COCC1=CC=CC(C(O)C=2N=C(OC)C=C(OC)N=2)=C1NS(=O)(=O)C(F)F NTBVTCXMRYKRTB-UHFFFAOYSA-N 0.000 description 2
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 2
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 2
- IWLMNTDYHCJTHA-UHFFFAOYSA-N OC1=C(C(=O)OCC)N=NN1CC1=CC=C(OC)C=C1 Chemical compound OC1=C(C(=O)OCC)N=NN1CC1=CC=C(OC)C=C1 IWLMNTDYHCJTHA-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005587 Oryzalin Substances 0.000 description 2
- WFVUIONFJOAYPK-KAMYIIQDSA-N Oxabetrinil Chemical compound C=1C=CC=CC=1C(/C#N)=N\OCC1OCCO1 WFVUIONFJOAYPK-KAMYIIQDSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000005591 Pendimethalin Substances 0.000 description 2
- WGVWLKXZBUVUAM-UHFFFAOYSA-N Pentanochlor Chemical compound CCCC(C)C(=O)NC1=CC=C(C)C(Cl)=C1 WGVWLKXZBUVUAM-UHFFFAOYSA-N 0.000 description 2
- 239000005593 Pethoxamid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 description 2
- 239000004349 Polyvinylpyrrolidone-vinyl acetate copolymer Substances 0.000 description 2
- RSVPPPHXAASNOL-UHFFFAOYSA-N Prodiamine Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O RSVPPPHXAASNOL-UHFFFAOYSA-N 0.000 description 2
- 239000005601 Propoxycarbazone Substances 0.000 description 2
- 239000005602 Propyzamide Substances 0.000 description 2
- 239000005603 Prosulfocarb Substances 0.000 description 2
- 239000005605 Pyraflufen-ethyl Substances 0.000 description 2
- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 description 2
- 239000005608 Quinmerac Substances 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 244000124765 Salsola kali Species 0.000 description 2
- 235000007658 Salsola kali Nutrition 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000002307 Solanum ptychanthum Species 0.000 description 2
- 235000000341 Solanum ptychanthum Nutrition 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 239000005621 Terbuthylazine Substances 0.000 description 2
- YIJZJEYQBAAWRJ-UHFFFAOYSA-N Thiazopyr Chemical compound N1=C(C(F)F)C(C(=O)OC)=C(CC(C)C)C(C=2SCCN=2)=C1C(F)(F)F YIJZJEYQBAAWRJ-UHFFFAOYSA-N 0.000 description 2
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005625 Tri-allate Substances 0.000 description 2
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 2
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000001356 alkyl thiols Chemical class 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- ORFLOUYIJLPLPL-WOJGMQOQSA-N alloxydim Chemical compound CCC\C(=N/OCC=C)C1=C(O)CC(C)(C)C(C(=O)OC)C1=O ORFLOUYIJLPLPL-WOJGMQOQSA-N 0.000 description 2
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 2
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 description 2
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 2
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 235000006263 bur ragweed Nutrition 0.000 description 2
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000021466 carotenoid Nutrition 0.000 description 2
- 150000001747 carotenoids Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 description 2
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 2
- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 2
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 description 2
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 2
- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 description 2
- DNUAYCRATWAJQE-UHFFFAOYSA-N flufenpyr-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(N2C(C(C)=C(C=N2)C(F)(F)F)=O)=C1F DNUAYCRATWAJQE-UHFFFAOYSA-N 0.000 description 2
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 2
- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical group C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical class CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- 230000002262 irrigation Effects 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 2
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229920005610 lignin Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 2
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 2
- RBNIGDFIUWJJEV-LLVKDONJSA-N methyl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-LLVKDONJSA-N 0.000 description 2
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 2
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 2
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 2
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 2
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 2
- 230000000394 mitotic effect Effects 0.000 description 2
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 231100001184 nonphytotoxic Toxicity 0.000 description 2
- GJQIMXVRFNLMTB-UHFFFAOYSA-N nonyl acetate Chemical compound CCCCCCCCCOC(C)=O GJQIMXVRFNLMTB-UHFFFAOYSA-N 0.000 description 2
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 235000014571 nuts Nutrition 0.000 description 2
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 2
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 2
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000005080 plant death Effects 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 2
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- IKVXBIIHQGXQRQ-CYBMUJFWSA-N propan-2-yl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-CYBMUJFWSA-N 0.000 description 2
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 2
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 2
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 2
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 2
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 2
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 2
- 235000009736 ragweed Nutrition 0.000 description 2
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 2
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 1
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- DQKWXTIYGWPGOO-UHFFFAOYSA-N (2,6-dibromo-4-cyanophenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=C(Br)C=C(C#N)C=C1Br DQKWXTIYGWPGOO-UHFFFAOYSA-N 0.000 description 1
- FHTLRVQASCAGSZ-UHFFFAOYSA-N (2-methylphenyl)sulfonylurea Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(N)=O FHTLRVQASCAGSZ-UHFFFAOYSA-N 0.000 description 1
- MPPOHAUSNPTFAJ-SECBINFHSA-N (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-SECBINFHSA-N 0.000 description 1
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 1
- DARPYRSDRJYGIF-PTNGSMBKSA-N (Z)-3-ethoxy-2-naphthalen-2-ylsulfonylprop-2-enenitrile Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(\C#N)=C/OCC)=CC=C21 DARPYRSDRJYGIF-PTNGSMBKSA-N 0.000 description 1
- USGUVNUTPWXWBA-JRIXXDKMSA-N (e,2s)-2-amino-4-(2-aminoethoxy)but-3-enoic acid Chemical compound NCCO\C=C\[C@H](N)C(O)=O USGUVNUTPWXWBA-JRIXXDKMSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 description 1
- DAGDLSRRQJATCV-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1OCCBr DAGDLSRRQJATCV-UHFFFAOYSA-N 0.000 description 1
- VQHHIQJPQOLZGF-UHFFFAOYSA-N 1-(2-iodophenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)I)=N1 VQHHIQJPQOLZGF-UHFFFAOYSA-N 0.000 description 1
- IAKGGJYLHBHSQD-UHFFFAOYSA-N 1-(azidomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CN=[N+]=[N-])C=C1 IAKGGJYLHBHSQD-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- AHXUVTKVCMOKIX-UHFFFAOYSA-N 1-bromo-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Br)C=C1 AHXUVTKVCMOKIX-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BXKKQFGRMSOANI-UHFFFAOYSA-N 1-methoxy-3-[4-[(2-methoxy-2,4,4-trimethyl-3h-chromen-7-yl)oxy]phenyl]-1-methylurea Chemical compound C1=CC(NC(=O)N(C)OC)=CC=C1OC1=CC=C2C(C)(C)CC(C)(OC)OC2=C1 BXKKQFGRMSOANI-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- KNGWEAQJZJKFLI-UHFFFAOYSA-N 2,2-dimethyl-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C)(C)OCC2=C1 KNGWEAQJZJKFLI-UHFFFAOYSA-N 0.000 description 1
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical class C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 description 1
- XTVIFVALDYTCLL-UHFFFAOYSA-N 2,3,5-trichloro-1h-pyridin-4-one Chemical compound ClC1=CNC(Cl)=C(Cl)C1=O XTVIFVALDYTCLL-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 1
- ROKVVMOXSZIDEG-UHFFFAOYSA-N 2-(3,5,6-trichloropyridin-2-yl)oxyacetate;triethylazanium Chemical compound CCN(CC)CC.OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl ROKVVMOXSZIDEG-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- WFZLCVIVTLLLCD-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methyl-1h-triazol-5-one Chemical compound N1C(=O)C(C)=NN1C1=CC=C(F)C=C1 WFZLCVIVTLLLCD-UHFFFAOYSA-N 0.000 description 1
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 1
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 1
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 description 1
- NQQBTWVFKDDVIB-UHFFFAOYSA-N 2-aminoethanol;3,6-dichloropyridine-2-carboxylic acid Chemical compound NCCO.OC(=O)C1=NC(Cl)=CC=C1Cl NQQBTWVFKDDVIB-UHFFFAOYSA-N 0.000 description 1
- IVDRCZNHVGQBHZ-UHFFFAOYSA-N 2-butoxyethyl 2-(3,5,6-trichloropyridin-2-yl)oxyacetate Chemical group CCCCOCCOC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl IVDRCZNHVGQBHZ-UHFFFAOYSA-N 0.000 description 1
- WKGKFWXGAHXMCE-UHFFFAOYSA-N 2-butoxyethyl 2-(4-chloro-2-methylphenoxy)acetate Chemical group CCCCOCCOC(=O)COC1=CC=C(Cl)C=C1C WKGKFWXGAHXMCE-UHFFFAOYSA-N 0.000 description 1
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 1
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
- MIJLZGZLQLAQCM-UHFFFAOYSA-N 2-ethoxyethyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCOCC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MIJLZGZLQLAQCM-UHFFFAOYSA-N 0.000 description 1
- IDGRPSMONFWWEK-UHFFFAOYSA-N 2-ethylhexyl 2-(4-chloro-2-methylphenoxy)acetate Chemical group CCCCC(CC)COC(=O)COC1=CC=C(Cl)C=C1C IDGRPSMONFWWEK-UHFFFAOYSA-N 0.000 description 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- UTWMSGSDWZDPOM-UHFFFAOYSA-N 2-methyl-3-phenylcyclobutan-1-one Chemical compound C1C(=O)C(C)C1C1=CC=CC=C1 UTWMSGSDWZDPOM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- UWLJERQTLRORJN-UHFFFAOYSA-N 3-(trifluoromethoxy)phenol Chemical compound OC1=CC=CC(OC(F)(F)F)=C1 UWLJERQTLRORJN-UHFFFAOYSA-N 0.000 description 1
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical class C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 description 1
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- VYXNMHWKULLWDK-UHFFFAOYSA-N 4-(bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]triazole Chemical compound FC(F)(F)OC1=CC=CC(OC=2C(=NN(N=2)C=2C=CC(=CC=2)C(F)(F)F)CBr)=C1 VYXNMHWKULLWDK-UHFFFAOYSA-N 0.000 description 1
- BCFOOQRXUXKJCL-UHFFFAOYSA-N 4-amino-4-oxo-2-sulfobutanoic acid Chemical class NC(=O)CC(C(O)=O)S(O)(=O)=O BCFOOQRXUXKJCL-UHFFFAOYSA-N 0.000 description 1
- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 1
- FZINIBTZNSPWQR-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=CC=N1 FZINIBTZNSPWQR-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- OYQSAEIWDLIZHC-UHFFFAOYSA-N 4-iodo-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(I)=CC=N1 OYQSAEIWDLIZHC-UHFFFAOYSA-N 0.000 description 1
- JFXFQTUTWWVHSN-UHFFFAOYSA-N 4-methoxy-2-[4-(trifluoromethyl)phenyl]-5-[[3-(trifluoromethyl)pyrazol-1-yl]methyl]triazole Chemical compound COC1=NN(C=2C=CC(=CC=2)C(F)(F)F)N=C1CN1C=CC(C(F)(F)F)=N1 JFXFQTUTWWVHSN-UHFFFAOYSA-N 0.000 description 1
- PYXNITNKYBLBMW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C1=CC=NN1 PYXNITNKYBLBMW-UHFFFAOYSA-N 0.000 description 1
- CYTOKNSEVPOFNF-UHFFFAOYSA-N 5-(trifluoromethyl)thiophen-3-one Chemical compound FC(F)(F)C1=CC(=O)CS1 CYTOKNSEVPOFNF-UHFFFAOYSA-N 0.000 description 1
- OPEJGICLTMWFNQ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-3-(3-methylthiophen-2-yl)-4h-1,2-oxazole Chemical compound C1=CSC(C=2CC(C)(COCC=3C(=CC=CC=3F)F)ON=2)=C1C OPEJGICLTMWFNQ-UHFFFAOYSA-N 0.000 description 1
- QQOGZMUZAZWLJH-UHFFFAOYSA-N 5-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-n-ethylsulfonyl-2-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)CC)=CC(OC=2C(=CC(=CC=2F)C(F)(F)F)Cl)=C1 QQOGZMUZAZWLJH-UHFFFAOYSA-N 0.000 description 1
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 1
- HZKBYBNLTLVSPX-UHFFFAOYSA-N 6-[(6,6-dimethyl-5,7-dihydropyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidene)amino]-7-fluoro-4-prop-2-ynyl-1,4-benzoxazin-3-one Chemical compound C#CCN1C(=O)COC(C=C2F)=C1C=C2N=C1SN=C2CC(C)(C)CN21 HZKBYBNLTLVSPX-UHFFFAOYSA-N 0.000 description 1
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 description 1
- WBFYVDCHGVNRBH-UHFFFAOYSA-N 7,8-dihydropteroic acid Chemical compound N=1C=2C(=O)NC(N)=NC=2NCC=1CNC1=CC=C(C(O)=O)C=C1 WBFYVDCHGVNRBH-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 241001103808 Albifimbria verrucaria Species 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000584608 Alternaria destruens Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000037005 Ambrosia artemisiifolia var. elatior Species 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000004535 Avena sterilis Nutrition 0.000 description 1
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 1
- 241000193755 Bacillus cereus Species 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001645380 Bassia scoparia Species 0.000 description 1
- 239000005471 Benfluralin Substances 0.000 description 1
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000005488 Bispyribac Substances 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 description 1
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- OVPOQARSILRTKD-UHFFFAOYSA-N COCCCn1c(ncc(C(=O)C2=C(O)CCCC2=O)c1=O)-c1cccc(OC)c1 Chemical compound COCCCn1c(ncc(C(=O)C2=C(O)CCCC2=O)c1=O)-c1cccc(OC)c1 OVPOQARSILRTKD-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 239000005490 Carbetamide Substances 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005647 Chlorpropham Substances 0.000 description 1
- 239000005498 Clodinafop Substances 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
- 241001529387 Colletotrichum gloeosporioides Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- 244000285774 Cyperus esculentus Species 0.000 description 1
- 240000001505 Cyperus odoratus Species 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical group COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000005506 Diclofop Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PHVNLLCAQHGNKU-UHFFFAOYSA-N Dimethipin Chemical compound CC1=C(C)S(=O)(=O)CCS1(=O)=O PHVNLLCAQHGNKU-UHFFFAOYSA-N 0.000 description 1
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 description 1
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- KCOCSOWTADCKOL-UHFFFAOYSA-N Ethidimuron Chemical compound CCS(=O)(=O)C1=NN=C(N(C)C(=O)NC)S1 KCOCSOWTADCKOL-UHFFFAOYSA-N 0.000 description 1
- 239000005512 Ethofumesate Substances 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 239000005513 Fenoxaprop-P Substances 0.000 description 1
- XDWSZOWLJIWERG-UHFFFAOYSA-N Fenuron-TCA Chemical compound [O-]C(=O)C(Cl)(Cl)Cl.C[NH+](C)C(=O)NC1=CC=CC=C1 XDWSZOWLJIWERG-UHFFFAOYSA-N 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 239000005530 Fluazifop-P Substances 0.000 description 1
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000005980 Gibberellic acid Substances 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 239000005565 Haloxyfop-P Substances 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- QBEXFUOWUYCXNI-UHFFFAOYSA-N Ioxynil octanoate Chemical compound CCCCCCCC(=O)OC1=C(I)C=C(C#N)C=C1I QBEXFUOWUYCXNI-UHFFFAOYSA-N 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 240000003978 Ipomoea coccinea Species 0.000 description 1
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- AZFKQCNGMSSWDS-UHFFFAOYSA-N MCPA-thioethyl Chemical group CCSC(=O)COC1=CC=C(Cl)C=C1C AZFKQCNGMSSWDS-UHFFFAOYSA-N 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 239000005576 Mecoprop-P Substances 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000003805 Musa ABB Group Nutrition 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 1
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- WHTBVLXUSXVMEV-UHFFFAOYSA-N Perfluidone Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 WHTBVLXUSXVMEV-UHFFFAOYSA-N 0.000 description 1
- 241000257649 Phalaris minor Species 0.000 description 1
- 241000233637 Phytophthora palmivora Species 0.000 description 1
- 235000008566 Pinus taeda Nutrition 0.000 description 1
- 241000218679 Pinus taeda Species 0.000 description 1
- 235000015266 Plantago major Nutrition 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- IPDFPNNPBMREIF-CHWSQXEVSA-N Prohydrojasmon Chemical compound CCCCC[C@@H]1[C@@H](CC(=O)OCCC)CCC1=O IPDFPNNPBMREIF-CHWSQXEVSA-N 0.000 description 1
- 241000578611 Puccinia thlaspeos Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 description 1
- 239000002167 Quinoclamine Substances 0.000 description 1
- 239000005609 Quizalofop-P Substances 0.000 description 1
- 239000005614 Quizalofop-P-ethyl Substances 0.000 description 1
- 239000005615 Quizalofop-P-tefuryl Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 235000008406 SarachaNachtschatten Nutrition 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- 239000004965 Silica aerogel Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000004790 Solanum aculeatissimum Nutrition 0.000 description 1
- 235000008424 Solanum demissum Nutrition 0.000 description 1
- 235000018253 Solanum ferox Nutrition 0.000 description 1
- 235000000208 Solanum incanum Nutrition 0.000 description 1
- 235000013131 Solanum macrocarpon Nutrition 0.000 description 1
- 235000009869 Solanum phureja Nutrition 0.000 description 1
- 235000017622 Solanum xanthocarpum Nutrition 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- FBPFZTCFMRRESA-NQAPHZHOSA-N Sorbitol Polymers OCC(O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-NQAPHZHOSA-N 0.000 description 1
- 241000209072 Sorghum Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000044578 Stenotaphrum secundatum Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- PHSUVQBHRAWOQD-UHFFFAOYSA-N Tiocarbazil Chemical compound CCC(C)N(C(C)CC)C(=O)SCC1=CC=CC=C1 PHSUVQBHRAWOQD-UHFFFAOYSA-N 0.000 description 1
- 239000005626 Tribenuron Substances 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 description 1
- FHOXQLTVOMNIOR-QZPAGEHASA-N [(1S,2R,4R,5S,7S,11S,12S,15R,16S)-2,16-dimethyl-15-[(1S)-1-[(2R,3R)-3-[(3S)-2-methylpentan-3-yl]oxiran-2-yl]ethyl]-8-oxo-4-propanoyloxy-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-5-yl] propanoate Chemical compound CC[C@@H](C(C)C)[C@H]1O[C@@H]1[C@@H](C)[C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)C[C@@H](OC(=O)CC)[C@@H](OC(=O)CC)C[C@@H]4C(=O)OC[C@H]3[C@@H]2CC1 FHOXQLTVOMNIOR-QZPAGEHASA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 description 1
- DBNLGTYGKCMLLR-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1 DBNLGTYGKCMLLR-UHFFFAOYSA-N 0.000 description 1
- ZCZSIDMEHXZRLG-UHFFFAOYSA-N acetic acid heptyl ester Natural products CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 208000014347 autosomal dominant hyaline body myopathy Diseases 0.000 description 1
- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 description 1
- QRSHQJLLXXEYPS-UHFFFAOYSA-N azane;5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 QRSHQJLLXXEYPS-UHFFFAOYSA-N 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- HYJSGOXICXYZGS-UHFFFAOYSA-N benazolin Chemical compound C1=CC=C2SC(=O)N(CC(=O)O)C2=C1Cl HYJSGOXICXYZGS-UHFFFAOYSA-N 0.000 description 1
- WQRCEBAZAUAUQC-UHFFFAOYSA-N benazolin-ethyl Chemical group C1=CC=C2SC(=O)N(CC(=O)OCC)C2=C1Cl WQRCEBAZAUAUQC-UHFFFAOYSA-N 0.000 description 1
- LVKBXDHACCFCTA-UHFFFAOYSA-N bencarbazone Chemical compound C1=C(C(N)=S)C(NS(=O)(=O)CC)=CC(N2C(N(C)C(=N2)C(F)(F)F)=O)=C1F LVKBXDHACCFCTA-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 238000010256 biochemical assay Methods 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000000853 biopesticidal effect Effects 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- RYVIXQCRCQLFCM-UHFFFAOYSA-N bispyribac Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(O)=O)=N1 RYVIXQCRCQLFCM-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- PSGPXWYGJGGEEG-UHFFFAOYSA-N butyl 9-hydroxyfluorene-9-carboxylate Chemical group C1=CC=C2C(C(=O)OCCCC)(O)C3=CC=CC=C3C2=C1 PSGPXWYGJGGEEG-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229950004243 cacodylic acid Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- NLKUPINTOLSSLD-UHFFFAOYSA-L calcium;4-(1-oxidopropylidene)-3,5-dioxocyclohexane-1-carboxylate Chemical compound [Ca+2].CCC([O-])=C1C(=O)CC(C([O-])=O)CC1=O NLKUPINTOLSSLD-UHFFFAOYSA-L 0.000 description 1
- 239000004490 capsule suspension Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- MXZACTZQSGYANA-UHFFFAOYSA-N chembl545463 Chemical compound Cl.C1=CC(OC)=CC=C1C(N=C1)=CN2C1=NC(C)=C2O MXZACTZQSGYANA-UHFFFAOYSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000003559 chemosterilizing effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- XXWNKVBJDWSYBN-UHFFFAOYSA-N diethoxy-phenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=CC=CC=C1 XXWNKVBJDWSYBN-UHFFFAOYSA-N 0.000 description 1
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229950010286 diolamine Drugs 0.000 description 1
- 150000004844 dioxiranes Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 239000004497 emulsifiable granule Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000000967 entomopathogenic effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- ZAKAONRTRWRIJT-UHFFFAOYSA-N ethyl 3-ethoxy-3-iminopropanoate Chemical compound CCOC(=N)CC(=O)OCC ZAKAONRTRWRIJT-UHFFFAOYSA-N 0.000 description 1
- XNKARWLGLZGMGX-UHFFFAOYSA-N ethyl 4-(4-chloro-2-methylphenoxy)butanoate Chemical group CCOC(=O)CCCOC1=CC=C(Cl)C=C1C XNKARWLGLZGMGX-UHFFFAOYSA-N 0.000 description 1
- PPXMGQIZAQMDDC-UHFFFAOYSA-N ethyl 5-chloro-1-[(4-methoxyphenyl)methyl]triazole-4-carboxylate Chemical compound ClC1=C(C(=O)OCC)N=NN1CC1=CC=C(OC)C=C1 PPXMGQIZAQMDDC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 230000004136 fatty acid synthesis Effects 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- YUVKUEAFAVKILW-SECBINFHSA-N fluazifop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-SECBINFHSA-N 0.000 description 1
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 description 1
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 description 1
- WFZSZAXUALBVNX-UHFFFAOYSA-N flufenpyr Chemical compound O=C1C(C)=C(C(F)(F)F)C=NN1C1=CC(OCC(O)=O)=C(Cl)C=C1F WFZSZAXUALBVNX-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- RSQSQJNRHICNNH-NFMPGMCNSA-N gibberellin A4 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@@]2(OC3=O)[C@H]1[C@@]3(C)[C@@H](O)CC2 RSQSQJNRHICNNH-NFMPGMCNSA-N 0.000 description 1
- SEEGHKWOBVVBTQ-NFMPGMCNSA-N gibberellin A7 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 SEEGHKWOBVVBTQ-NFMPGMCNSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 229940087559 grape seed Drugs 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 244000304962 green bristle grass Species 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- MJAWMRVEIWPJRW-UHFFFAOYSA-N haloxydine Chemical compound FC=1NC(F)=C(Cl)C(=O)C=1Cl MJAWMRVEIWPJRW-UHFFFAOYSA-N 0.000 description 1
- GOCUAJYOYBLQRH-MRVPVSSYSA-N haloxyfop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-MRVPVSSYSA-N 0.000 description 1
- JPXGPRBLTIYFQG-UHFFFAOYSA-N heptan-4-yl acetate Chemical compound CCCC(CCC)OC(C)=O JPXGPRBLTIYFQG-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- VDEGQTCMQUFPFH-UHFFFAOYSA-N hydroxy-dimethyl-arsine Natural products C[As](C)O VDEGQTCMQUFPFH-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- 229940046817 hypophosphorus acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- DBTNVRCCIDISMV-UHFFFAOYSA-L lithium;magnesium;propane;dichloride Chemical compound [Li+].[Mg+2].[Cl-].[Cl-].C[CH-]C DBTNVRCCIDISMV-UHFFFAOYSA-L 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- UMCKXPWHWSKWJJ-UHFFFAOYSA-N n,n-dimethyl-2-oxo-6-(trifluoromethyl)-1h-pyridine-3-carboxamide Chemical compound CN(C)C(=O)C1=CC=C(C(F)(F)F)N=C1O UMCKXPWHWSKWJJ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- GBHVIWKSEHWFDD-UHFFFAOYSA-N n-[2-(4,6-dimethoxy-1,3,5-triazine-2-carbonyl)-6-fluorophenyl]-1,1-difluoro-n-methylmethanesulfonamide Chemical compound COC1=NC(OC)=NC(C(=O)C=2C(=C(F)C=CC=2)N(C)S(=O)(=O)C(F)F)=N1 GBHVIWKSEHWFDD-UHFFFAOYSA-N 0.000 description 1
- CHEDHKBPPDKBQF-UPONEAKYSA-N n-[5-[(6s,7ar)-6-fluoro-1,3-dioxo-5,6,7,7a-tetrahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-4-fluorophenyl]-1-chloromethanesulfonamide Chemical compound N1([C@@H](C2=O)C[C@@H](C1)F)C(=O)N2C1=CC(NS(=O)(=O)CCl)=C(Cl)C=C1F CHEDHKBPPDKBQF-UPONEAKYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- MNSHGRXIICSKRQ-UHFFFAOYSA-L nickel(2+);3-oxobutanoate Chemical compound [Ni+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O MNSHGRXIICSKRQ-UHFFFAOYSA-L 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- YOCBOYPGZVFUCQ-UHFFFAOYSA-L nickel(2+);tricyclohexylphosphane;dichloride Chemical compound Cl[Ni]Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 YOCBOYPGZVFUCQ-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- ORHJUFUQMQEFPQ-UHFFFAOYSA-M potassium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [K+].CC1=CC(Cl)=CC=C1OCC([O-])=O ORHJUFUQMQEFPQ-UHFFFAOYSA-M 0.000 description 1
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- ZKWPMZVVAJSYNI-UHFFFAOYSA-N prop-2-enal Chemical compound C=CC=O.C=CC=O ZKWPMZVVAJSYNI-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical class C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical compound [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 210000002377 thylakoid Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXPZOKVSFMRGMQ-UHFFFAOYSA-N trifluoromethylcyclohexane Chemical compound FC(F)(F)C1CCCCC1 QXPZOKVSFMRGMQ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Definitions
- This invention relates to certain triazoles, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.
- the control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safe or have different sites of action.
- This invention is directed to compounds of Formula 1 (including all stereoisomers), including N-oxides and salts thereof, agricultural compositions containing them and their use as herbicides:
- R 1 is halogen, cyano, C 1 -C4 alkoxy, C1 -C4 haloalkoxy, C2-C4 alkoxyalkyl, C1 -C4 alkyl, C 1 -C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-Cg alkylcarbonyloxy, Ci -C4 hydroxyalkyl, SO n (R 12 ), C2-C4 alkylthioalkyl, C2-C4 alkylsulfonylalkyl, C 1 -C4 alkylamino C2-C4 dialkylamino, C3-C6 cycloalkyl or hydroxy;
- A is a radical selected from the roup consisting of
- each Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently N or CR 2 , provided no more than 3 of
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are N;
- each Y 6 , Y 7 and Y 8 is independently N or CR 3 , provided no more than 2 of Y 6 , Y 7 and
- Y 8 are N;
- Z is O or S
- Q is C(R 4 )(R 5 ), O, S or NR 6 ;
- J is phenyl substituted with 1 R 7 and optionally substituted with up to 2 R 8 ;
- J is a 6-membered aromatic heterocyclic ring substituted with 1 R 7 and optionally substituted with up to 2 R 8 on carbon ring members;
- J is a 5-membered aromatic heterocyclic ring substituted with 1 R 9 on carbon ring members and R 1 1 on nitrogen ring members; and optionally substituted with 1
- each R 2 is independently H, halogen, cyano, nitro, SF 5 , -C4 alkoxy, -C4
- haloalkoxy C1-C4 alkyl, -C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy or S(0) n R 12 ;
- each R 3 is independently H, halogen, cyano, C1-C4 alkyl, -C4 haloalkyl, C1-C4 alkoxy, -C4 haloalkoxy or S(0) n R 12 ;
- R 4 is H, F, CI, Br, cyano, C r C 4 alkyl, C r C 4 haloalkyl or C0 2 R 13 ;
- R 5 is H, F, C r C 4 alkyl, OH or OR 13 ; or
- R 4 and R 5 are taken together with the carbon to which they are attached to form
- R 6 is H, C r C 4 alkyl or C r C 4 haloalkyl
- R 7 is halogen, cyano, SF 5 , -C4 alkyl, C1-C4 haloalkyl, -C4 alkoxy, C1-C4
- each R 8 is independently halogen, cyano, -C4 alkyl, -C4 haloalkyl, -C4 alkoxy,
- R 7 and R 8 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms;
- R 9 is halogen, cyano, SF 5 , -C4 alkyl, C1-C4 haloalkyl, -C4 alkoxy, C1-C4
- R 10 is halogen, cyano, C1-C4 alkyl, -C4 haloalkyl, -C4 alkoxy, -C4 haloalkoxy or S(0) n Rl 2 ;
- R 1 1 is C r C 4 alkyl or C r C 4 haloalkyl
- each R 12 is independently C1-C4 alkyl or 1-C4 haloalkyl
- each R 13 is independently H or C1-C4 alkyl
- R 14 is C1-C4 alkyl or C r C 4 haloalkyl
- R 15 is Ci -C4 alkyl or Ci -C4 haloalkyl
- each n is independently 0, 1 or 2;
- R 1 is CH 3 ;
- A is A-l ;
- Y 1 , Y 2 , Y 3 and Y 4 are each CH; and
- Y 5 is CCF 3 then J is other than 3-chloro-lH-l ,2,4-thiadiazol-5-yl, 4-fluoro-2-pyridinyl,
- R 1 is CH 3 ;
- A is A-l ;
- Y 1 , Y 2 , Y 3 and Y 4 are each CH; and
- Y 5 is CF then J is other than 4-fluoro-3-methylphenyl.
- this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof.
- This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).
- This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) through (bl6); and salts of compounds of (bl) through (bl6).
- composition, mixture, process, method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
- transitional phrase consisting essentially of is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
- the term “seedling”, used either alone or in a combination of words means a young plant developing from the embryo of a seed.
- the term “broadleaf used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
- the term “alkylating reagent” refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon- containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R 1 .
- alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers.
- cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
- Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl isomers.
- Alkenyl also includes polyenes such as 1 ,2-propadienyl 1,3-butadienyl.
- Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl and pentynyl isomers.
- Alkynyl can also include moieties comprised of multiple triple bonds such as 1,3-butadiynyl.
- Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
- Alkoxyalkyl denotes alkoxy substitution on alkyl.
- alkoxyalkyl include CH3OCH2, CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
- Alkynyloxy includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC ⁇ CCH 2 0 and CH 3 C ⁇ CCH 2 0.
- Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio and the different propylthio, butylthio isomers. "Alkylthioalkyl” denotes alkylthio substitution on alkyl.
- alkylthioalkyl examples include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
- alkylsulfonyl examples include CH 3 S(0) 2 -, CH 3 CH 2 S(0) 2 - and CH 3 CH 2 CH 2 S(0) 2 -, and the different butylsulfonyl isomers.
- alkylsulfonylalkyl denotes alkylsulfonyl substitution on alkyl.
- alkylsulfonylalkyl examples include CH 3 S0 2 CH 2 , CH 3 S0 2 CH 2 CH 2 , CH 3 CH 2 S0 2 CH 2 and CH 3 CH 2 S0 2 CH 2 CH 2 .
- Alkylthioalkoxy denotes alkylthio substitution on alkoxy.
- Hydroxyalkyl denotes an alkyl group substituted with one hydroxy group. Examples of hydroxy alkyl include HOCH 2 CH 2 CH 2 -, CH 3 CH 2 CH(OH)CH 2 -, and CH 3 CH 2 CHOH-.
- Alkylamino dialkylamino
- dialkylamino are defined analogously to the above examples.
- halogen either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F 3 C-, C1CH 2 -, CF 3 CH 2 - and CF 3 CC1 2 -.
- haloalkoxy and the like, is defined analogously to the term “haloalkyl”.
- haloalkoxy include CF 3 0-, CC1 3 CH 2 0-, HCF 2 CH 2 CH 2 0- and CF 3 CH 2 0-.
- C1-C4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl
- C 2 alkoxyalkyl designates CH 3 OCH 2 -
- C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 )-, CH 3 OCH 2 CH 2 - or CH 3 CH 2 OCH 2 -
- C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 - and CH 3 CH 2 OCH 2 CH 2 -.
- a group contains a substituent which can be hydrogen, for example R 2 , R 3 , R 4 , R 5 and R 6 , then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
- a variable group is shown to be optionally attached to a position, for example R 8 , then hydrogen may be at the position even if not recited in the variable group definition.
- hydrogen atoms are attached to take up any free valency.
- a “ring” as a component of Formula 1 is heterocyclic.
- the term “ring member” refers to an atom or other moiety forming the backbone of a ring.
- the term “heterocyclic ring” denotes a ring in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring.
- heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.”
- Aromatic indicates that each of the ring atoms is essentially in the same plane and has a / ⁇ -orbital perpendicular to the ring plane, and that (4n + 2) ⁇ electrons, where n is a positive integer, are associated with the ring to comply with Huckel's rule.
- optionally substituted in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated.
- optionally substituted is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted.” Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.
- J When J is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 though any available carbon or nitrogen ring atom, unless otherwise described.
- J can be (among others) phenyl optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention.
- An example of phenyl optionally substituted with one to five substituents is the ring illustrated as U-l in Exhibit 1 , wherein R v is R 7 and R 8 as defined in the Summary of the Invention for substitution on J and r is an integer from 0 to 3 (i.e. substituted with one R 7 and up to two R 8 ).
- J can be phenyl or a 5- or 6-membered aromatic heterocyclic ring, which may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention.
- a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings U-2 through U-61 illustrated in Exhibit 1 wherein R v is any substituent as defined in the Summary of the Invention for J (i.e. R 7 , R 8 , R 9 , R 10 and R 1 !) and r is an integer from 0 to 3, limited by the number of available positions on each U group.
- U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, for these U groups r is limited to the integers 0 or 1 , and r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (R v ) r .
- J is a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention for J
- one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.
- Examples of a 5-membered carbocyclic ring containing ring members selected from up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms includes the rings G-l through G-5 as illustrated in Exhibit 2 (i.e. when R 7 and R 8 are taken together with two adjacent carbon atoms). Note that when the attachment point on the R v group is illustrated as floating, the R v group can be attached to the remainder of Formula 1 through any available carbon G group by replacement of a hydrogen atom. The optional substituents corresponding to R v can be attached to any available carbon or nitrogen by replacing a hydrogen atom.
- r is typically an integer from 0 to 5, limited by the number of available positions on each G group.
- Compounds of this invention can exist as one or more stereoisomers.
- the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
- one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
- the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
- Non- crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
- Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
- polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
- polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
- a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1.
- Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
- nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides.
- nitrogen-containing heterocycles which can form N-oxides.
- tertiary amines can form N-oxides.
- N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
- MCPBA peroxy acids
- alkyl hydroperoxides such as t-butyl hydroperoxide
- sodium perborate sodium perborate
- dioxiranes such as dimethyldioxirane
- salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms.
- the salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
- salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
- Embodiments of the present invention as described in the Summary of the Invention include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof) the following:
- Embodiment 1 A compound of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Invention.
- Embodiment 1A A compound of Formula 1 wherein R 1 is H, halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, -C4 haloalkyl, C - C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 hydroxyalkyl, SO n (R 12 ), C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfonylalkyl, C r C 4 alkylamino or C2-C4 dialkylamino.
- R 1 is H, halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, -C
- Embodiment IB A compound of Embodiment 1A wherein R 1 is other than H, Embodiment 1C.
- Embodiment 2 A compound of Embodiment 1 or 1C wherein R 1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, -C4 haloalkyl, C2- C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 hydroxyalkyl, SO n (R 12 ), C 2 -C 4 alkylthioalkyl or C 2 -C 4 alkylsulfonylalkyl.
- Embodiment 3 A compound of Embodiment 1 or 1C wherein R 1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, -C4 haloalkyl, C2- C
- Embodiment 4 A compound of Embodiment 3 wherein R 1 is halogen, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C2-C4 alkoxyalkyl, C 1 -C4 alkyl or C 1 -C4 haloalkyl.
- Embodiment 5 A compound of Embodiment 4 wherein R 1 is C 1 -C4 alkoxy, C1 -C4 haloalkoxy or Ci -C4 alkyl.
- Embodiment 6 A compound of Embodiment 5 wherein R 1 is C i -C4 alkoxy or Ci -C4 alkyl.
- Embodiment 7 A compound of Embodiment 6 wherein R 1 is C 1 -C4 alkyl.
- Embodiment 7A A compound of Embodiment 7 wherein R 1 is Ci -C3 alkyl.
- Embodiment 7B A compound of Embodiment 7 wherein R 1 is C 1 -C2 alkyl.
- Embodiment 8 A compound of Embodiment 7 wherein R 1 is CH3.
- Embodiment 8A A compound of Embodiment 5 wherein R 1 is CH3CH2O-, CH3O-, CF 3 CH 2 0- or CH 3 .
- Embodiment 8B A compound of Embodiment 5 wherein R 1 is CH3CH2O-, CH3O- or CH 3 .
- Embodiment 8C A compound of Embodiment 5 wherein R 1 is CH3CH2O- or CH3O-, Embodiment 8D. A compound of Embodiment 5 wherein R 1 is CH3CH2O-.
- Embodiment 9 A compound of any one of Embodiments 1 through 8D wherein A is a radical selected from the group consisting of A-l and A-2.
- Embodiment 10 A compound of Embodiment 9 wherein A is A-l .
- Embodiment 11 A compound of Embodiment 10 wherein each Y 1 , Y 3 , Y 4 and Y 5 is independently N or CR 2 ; and Y 2 is CR 2 .
- Embodiment 12 A compound of Embodiment 11 wherein each Y 1 and Y 5 is
- each Y 2 , Y 3 and Y 4 is CR 2 .
- Embodiment 13 A compound of Embodiment 12 wherein Y 1 is N or CR 2 ; and each
- Y 2 , Y 3 , Y 4 and Y 5 is independently CR 2 .
- Embodiment 14 A compound of Embodiment 13 wherein Y 1 is N; and each Y 2 , Y 3 , Y 4 and Y 5 is independently CR 2 .
- Embodiment 15 A compound of Embodiment 14 wherein Y 1 is N; each Y 2 , Y 3 and
- Y 4 is CH; and Y 5 is CF.
- Embodiment 16 A compound of Embodiment 13 wherein each Y 1 , Y 2 , Y 3 and Y 4 and is CH; and Y 5 is CCF 3 or CF.
- Embodiment 17 A compound of Embodiment 9 wherein A is A-2.
- Embodiment 18 A compound of Embodiment 17 wherein each Y 6 and Y 7 is
- Embodiment 19 A compound of Embodiment 18 wherein each Y 6 and Y 7 is N; and Y 8 is CR 3 .
- Embodiment 20 A compound of Embodiment 19 wherein each Y 6 and Y 7 is N; and Y 8 is CH.
- Embodiment 21 A compound of any one of Embodiments 1 through 9 or 17 through 20 wherein Z is S.
- Embodiment 22 A compound of any one of Embodiments 1 through 21 wherein Q is C(R 4 )(R 5 ), O or S.
- Embodiment 23 A compound of Embodiment 22 wherein Q is C(R 4 )(R 5 ) or O.
- Embodiment 24 A compound of Embodiment 23 wherein Q is C(R 4 )(R 5 ).
- Embodiment 25 A compound of Embodiment 23 wherein Q is O.
- Embodiment 26 A compound of any one of Embodiments 1 through 25 wherein J is selected from
- t 0, 1 or 2;
- u is 0 or 1.
- Embodiment 27 A compound of Embodiment 26 wherein J is selected from J-1
- Embodiment 28 A compound of Embodiment 26 wherein J is selected from J- 15 through J-33(i.e. J is a 5-membred aromatic heterocyclic ring selected from J-15 through J-33).
- Embodiment 29 A compound of Embodiment 26 wherein J is selected from J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-9, J-12, J-17, J-18, J-20, J-22, J-26, J-29 and J-30 (i.e. all
- Embodiment 30 A compound of Embodiment 27 or 29 wherein J is selected from J-1,
- J-2, J-3, J-4, J-5, J-6, J-7, J-9 and J-12 i.e. all 6-membered J groups prepared in
- Embodiment 3 OA A compound of Embodiment 27 or 29 wherein J is selected from
- Embodiment 3 OB A compound of Embodiment 27 or 29 wherein J is selected from
- Embodiment 31 A compound of Embodiment 28 or 29 wherein J is selected from J-18, J-20, J-22, J-26, J-29 and J-30 (i.e. all 5-membered J groups prepared in
- Embodiment 31 A A compound of Embodiment 28 or 29 wherein J is selected from J-15, J-21, J-22, J-23, J-24, J-25, J-26, J-27, J-28, J-31 and J-33 (i.e. all nitrogen containing 5-membered J groups linked through carbon).
- Embodiment 3 IB A compound of Embodiment 28 or 29 wherein J is selected from
- J-16, J-17, J-18, J-19, J-20 and J-32 i.e. all nitrogen containing 5-membered J groups linked through nitrogen.
- Embodiment 32 A compound of Embodiment 26 wherein J is selected from J-1, J-2, J-10, J-17, J-18 and J-20.
- Embodiment 33 A compound of Embodiment 32 wherein J is selected from J-1, J-2,
- Embodiment 34 A compound of Embodiment 33 wherein J is J-1.
- Embodiment 35 A compound of Embodiment 33 wherein J is J-2.
- Embodiment 35 A A compound of any one of Embodiments 26, 27, 29, 30, 30A, 30B, 32 or 33 wherein t is 0 or 1.
- Embodiment 35B A compound of Embodiment 35 A wherein t is 0.
- Embodiment 35C A compound of any one of Embodiments 26, 28, 29, 31, 31A, 31B, 32 or 33 wherein u is 0.
- Embodiment 36 A compound of any one of Embodiments 1 through 26, 27, 29, 30 or 32 through 34 wherein J is other than J-1.
- Embodiment 37 A compound of any one of Embodiments 1 through 36 wherein each R 2 is independently H, halogen, -C4 alkoxy, -C4 alkyl or C1-C4 haloalkyl.
- Embodiment 38 A compound of Embodiment 37 wherein each R 2 is independently H, halogen, C 1 -C4 alkyl or C 1 -C4 haloalkyl.
- Embodiment 39 A compound of Embodiment 38 wherein each R 2 is independently H,
- Embodiment 40 A compound of Embodiment 39 wherein each R 2 is independently H,
- Embodiment 41 A compound of Embodiment 40 wherein each R 2 is independently H or CF 3 .
- Embodiment 42 A compound of Embodiment 40 wherein each R 2 is independently H or F.
- Embodiment 43 A compound of any one of Embodiments 1 through 42 wherein each
- R 3 is independently H, halogen or C1 -C4 haloalkyl.
- Embodiment 44 A compound of Embodiment 43 wherein each R 3 is independently H,
- Embodiment 45 A compound of Embodiment 44 wherein each R 3 is independently H or CF 3 .
- Embodiment 45 A A compound of any one of Embodiments 1 through 45 wherein R 4 is taken alone.
- Embodiment 46 A compound of any one of Embodiments 1 through 45 A wherein R 4 is H, F, CI, Br or C r C 4 alkyl.
- Embodiment 47 A compound of Embodiment 46 wherein R 4 is H, F or CH 3 .
- Embodiment 48 A compound of Embodiment 47 wherein R 4 is H.
- Embodiment 48 A A compound of any one of Embodiments 1 through 48 wherein R 5 is taken alone.
- Embodiment 49 A compound of any one of Embodiments 1 through 48A wherein R 5 is H, F or OH.
- Embodiment 50 A compound of Embodiment 49 wherein R 5 is H or F.
- Embodiment 51 A compound of Embodiment 50 wherein R 5 is H.
- Embodiment 52 A compound of Embodiment 50 wherein R 5 is F.
- Embodiment 53 A compound of any one of Embodiments 1 through 45 wherein R 4 and R 5 are taken together with the carbon to which they are attached to form
- Embodiment 54 A compound of any one of Embodiments 1 through 53 wherein R 6 is H or C r C 4 alkyl.
- Embodiment 55 A compound of Embodiment 54 wherein R 6 is CH 3 .
- Embodiment 56 A compound of Embodiment 54 wherein R 6 is H.
- Embodiment 56 A A compound of any one of Embodiments 1 through 56 wherein R 7 is taken alone.
- Embodiment 57 A compound of any one of Embodiments 1 through 56A wherein R 7 is halogen, Ci -C4 alkyl, Ci -C4 haloalkyl, C 1 -C4 alkoxy or Ci -C4 haloalkoxy.
- Embodiment 58 A compound of Embodiment 57 wherein R 7 is halogen, C 1 -C4 alkyl or C 1 -C4 haloalkyl.
- Embodiment 59 A compound of Embodiment 58 wherein R 7 is F, CH3 or CF3.
- Embodiment 60 A compound of Embodiment 59 wherein R 7 is F or CF3.
- Embodiment 61 A compound of Embodiment 60 wherein R 7 is F.
- Embodiment 62 A compound of Embodiment 60 wherein R 7 is CF3.
- Embodiment 62A A compound of any one of Embodiments 1 through 62 wherein each R 8 is taken alone.
- Embodiment 63 A compound of any one of Embodiments 1 through 62A wherein each R 8 is independently halogen or Ci -C4 haloalkyl.
- Embodiment 64 A compound of Embodiment 63 wherein each R 8 is independently F,
- Embodiment 65 A compound of Embodiment 63 wherein each R 8 is F.
- Embodiment 66 A compound of any one of Embodiments 1 through 56 wherein R 7 and R 8 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms.
- Embodiment 67 A compound of Embodiment 66 wherein R 7 and R 8 are taken
- Embodiment 68 A compound of Embodiment 67 wherein R 7 and R 8 are taken
- Embodiment 69 A compound of Embodiment 68 wherein R 7 and R 8 are taken
- J-1B Embodiment 70 A compound of any one of Embodiments 1 through 69 wherein R 9 is halogen, Ci -C4 alkyl, Ci -C4 haloalkyl, Ci -C4 alkoxy or Ci -C4 haloalkoxy.
- Embodiment 71 A compound of Embodiment 70 wherein R 9 is halogen, C 1 -C4 alkyl Ci -C4 haloalkyl or Ci -C4 alkoxy.
- Embodiment 72 A compound of Embodiments 71 wherein R 9 is halogen, Ci -C4 alkyl or C 1 -C4 haloalkyl.
- Embodiment 73 A compound of Embodiment 72 wherein R 9 is F, CH3 or CF3.
- Embodiment 74 A compound of Embodiment 73 wherein R 9 is F or CF3.
- Embodiment 75 A compound of Embodiment 74 wherein R 9 is F.
- Embodiment 76 A compound of Embodiment 74 wherein R 9 is CF3.
- Embodiment 77 A compound of any one of Embodiments 1 through 76 wherein R 10 is halogen, Ci -C4 alkyl, Ci -C4 haloalkyl, C 1 -C4 alkoxy or Ci -C4 haloalkoxy.
- Embodiment 78 A compound of Embodiment 77 wherein R 10 is halogen, C 1 -C4 alkyl or C 1 -C4 haloalkyl.
- Embodiment 79 A compound of Embodiment 78 wherein R 10 is F, CH3 or CF3.
- Embodiment 80. A compound of Embodiment 79 wherein R 10 is F or CF3.
- Embodiment 81 A compound of Embodiment 80 wherein R 10 is F.
- Embodiment 82 A compound of Embodiment 80 wherein R 10 is CF3.
- Embodiment 83 A compound of any one of Embodiments 1 through 82 wherein R 1 1 is C 1 -C4 alkyl or C 1 -C4 haloalkyl.
- Embodiment 84 A compound of Embodiment 83 wherein R 1 1 is C 1 -C4 alkyl.
- Embodiment 85 A compound of Embodiment 84 wherein R 1 1 is CH3.
- Embodiment 86 A compound of any one of Embodiments 1 through 85 wherein each
- R 12 is independently Ci -C4 alkyl.
- Embodiment 87 A compound of Embodiment 86 wherein each R 12 is CH3.
- Embodiment 88 A compound of any one of Embodiments 1 through 87 wherein each
- R 13 is independently CH 3 or CH 2 CH 3 .
- Embodiment 89 A compound of Embodiment 88 wherein each R 13 is CH3.
- Embodiment 90 A compound of any one of Embodiments 1 through 89 wherein R 14 is C 1 -C4 alkyl.
- Embodiment 91 A compound of Embodiment 90 wherein R 1 is CH3.
- Embodiment 92 A compound of any one of Embodiments 1 through 91 wherein R 15 is C 1 -C4 alkyl.
- Embodiment 93 A compound of Embodiment 92 wherein R 15 is CH3.
- Embodiment 94 A compound of any one of Embodiments 1 through 93 wherein n is 0 or 2.
- Embodiment 95 A compound of Embodiment 94 wherein n is 0.
- Embodiment 96 A compound of Embodiment 94 wherein n is 2.
- Embodiments of this invention, including Embodiments 1-96 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1.
- embodiments of this invention, including Embodiments 1-96 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
- Embodiment A A compound of the Summary of the Invention wherein
- R 1 is halogen, C 1 -C4 alkoxy, C1 -C4 haloalkoxy, C2-C4 alkoxyalkyl, C 1 -C4 alkyl, C1 -C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy,
- A is a radical selected from the group consisting of A-l and A-2;
- each Y 1 , Y 3 , Y 4 and Y 5 is independently N or CR 2 ; and Y 2 is CR 2 ;
- each Y 6 and Y 7 is independently N or CR 3 ; and Y 8 is CR 3 ;
- Q is C(R 4 )(R 5 ), O or S;
- J is selected from J-l through J-33;
- t 0, 1 or 2;
- each R 2 is independently H, halogen, Ci -C4 alkoxy, Ci -C4 alkyl or Ci -C4 haloalkyl; each R 3 is independently H, halogen or Ci -C4 haloalkyl
- R 4 is H, F, CI, Br or C r C 4 alkyl
- R 5 is H, F or OH
- R 7 is halogen, Ci -C4 alkyl, Ci -C4 haloalkyl, Ci -C4 alkoxy or Ci -C4 haloalkoxy;
- R 8 is independently halogen or Ci -C4 haloalkyl
- R 7 and R 8 are taken together with two adjacent carbon atoms to form a
- R 9 is halogen, Ci -C4 alkyl, Ci -C4 haloalkyl, Ci -C4 alkoxy or Ci -C4 haloalkoxy;
- R 10 is halogen, C 1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy or C1 -C4 haloalkoxy;
- R 1 1 is C r C 4 alkyl or C r C 4 haloalkyl
- each R 1 is independently C 1 -C4 alkyl
- each R 1 is independently CH 3 or CH2CH3;
- R 14 is C1-C4 alkyl
- R 15 is C r C 4 alkyl
- n 0 or 2.
- Embodiment B A compound of Embodiment A wherein R 1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl or C2-C4 alkenyl;
- each Y 1 and Y 5 is independently N or CR 2 ; and each Y 2 , Y 3 and Y 4 is CR 2 ;
- each Y 6 and Y 7 is N; and Y 8 is CR 3 ;
- Q is C(R 4 )(R 5 ) or O
- J is selected from J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-9, J-12, J-17, J-18, J-20, J-22, J-26,
- t is 0 or 1 ;
- each R 2 is independently H, halogen, Ci -C4 alkyl or Ci -C4 haloalkyl;
- each R 3 is independently H, F, CI or CF 3 ;
- R 4 is H, F or CH 3 ;
- R 5 is H or F
- R 7 is F, CH 3 or CF 3 ;
- R 8 is independently F, CI or CF 3 ;
- R 9 is halogen, C1-C4 alkyl or C1-C4 haloalkyl
- R 10 is halogen, C1-C4 alkyl or C1-C4 haloalkyl
- R 11 isC r C 4 alkyl
- each R 1 is CH 3 ;
- eachR 13 isCH 3 .
- Embodiment C A compound of Embodiment A wherein
- R 1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl or Ci -C4 haloalkyl;
- A is A-l
- Y 1 is N or CR 2 ; and each Y 2 , Y 3 , Y 4 and Y 5 is independently CR 2 ;
- J is selected from J-1, J-2, J- 10, J-17, J-18 and J-20;
- each R 2 is independently H, F, CI, CH 3 or CF 3 ;
- R 4 is H
- R 5 is H
- R 7 is For CF 3 .
- Embodiment D A compound of Embodiment B wherein
- R 1 is C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkyl
- A is A-l
- Y 1 is N or CR 2 ; and each Y 2 , Y 3 , Y 4 and Y 5 is independently CR 2 ;
- J is selected from J-1, J-2, J-17 and J-18; each R 2 is independently H, F, CI or CF 3 ; and
- R 7 is CF 3 .
- Embodiment E A compound of Embodiment D wherein
- R 1 is CH 3 ;
- each Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently CR 2 ;
- each R 2 is independently H or F.
- Specific embodiments include compounds of Formula 1 selected from the group consisting of:
- Specific embodiments also include compounds of Formula 1 selected from the group consisting of:
- Specific embodiments also include compounds of Formula 1 selected from the group consisting of:
- This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein).
- the compounds of the invention e.g., as a composition described herein.
- embodiments relating to methods of use are those involving the compounds of embodiments described above.
- Compounds of the invention are particularly useful for selective control of weeds in cereal crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.
- herbicidal compositions of the present invention comprising the compounds as described in the embodiments above.
- This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics and (b5) 5 -enol-pyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (blO) auxin transport inhibitors, (bl 1) phytoene desaturase (PDS) inhibitors, (bl2) 4-hydroxyphenyl-pyruv
- Photosystem II inhibitors are chemical compounds that bind to the D-l protein at the Qfl-binding niche and thus block electron transport from to QB in the chloroplast thylakoid membranes.
- the electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction.
- the QB-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
- binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil
- binding site B binds the phenylureas such as diuron
- binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
- photosystem II inhibitors include ametryn, atrazine, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor, bromof
- AH AS inhibitors are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for DNA synthesis and cell growth.
- AHAS acetohydroxy acid synthase
- ALS acetolactate synthase
- AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl (b2a), chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (b2b), flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfos
- ACCase inhibitors are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back.
- ACCase inhibitors include cyclopyrimorate, clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, profoxydim, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.
- auxin is a plant hormone that regulates growth in many plant tissues.
- auxin mimics are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species.
- auxin mimics include aminocyclopyrachlor and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen, halauxifen-methyl, mecoprop, MCPA, MCPB, 2,3,6-TBA, picloram, triclopyr, quinclorac and quinmerac.
- EEPSP (5 -enol-pyruvylshikimate-3 -phosphate) synthase inhibitors) are chemical compounds that inhibit the enzyme, 5 -enol-pyruvylshikimate-3 -phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine.
- EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points.
- Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group.
- Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
- Photosystem I electron diverters are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles "leak", leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include paraquat and diquat.
- PPO inhibitors are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out.
- PPO inhibitors include acifluorfen-sodium, bifenox, chlomethoxyfen, fluoroglycofen-ethyl, fomesafen, halosafen, lactofen, oxyfluorfen, fluazolate, pyraflufen-ethyl, cinidon-ethyl, flumioxazin, flumiclorac-pentyl, fluthiacet-methyl, thidiazimin, oxadiazon, oxadiargyl, saflufencil, azafenidin, carfentrazone carfentrazone-ethyl, sulfentrazone, pentoxazone, benzfendizone, butafenacil
- GS (glutamine synthase) inhibitors are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes.
- the GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P and bilanaphos.
- VLCFA very long chain fatty acid
- elongase inhibitors are herbicides having a wide variety of chemical structures, which inhibit the elongase.
- Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs.
- very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains.
- Such herbicides include acetochlor, alachlor, butachlor, dimethachlor, dimethanamid, metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor, diphenamid, napropamide, naproanilide, fenoxasulfone, flufenacet, indanofan, mefenacet, fentrazamide, anilofos, cafenstrole, piperophos including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides.
- auxin transport inhibitors are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein.
- auxin transport inhibitors include naptalam (also known as N-(l-naphthyl)phthalamic acid and 2-[(l-naphthalenylamino)carbonyl]benzoic acid) and diflufenzopyr.
- PDS phytoene desaturase inhibitors
- bl l are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step.
- PDS inhibitors include norflurzon, diflufenican, picolinafen, beflubutamide, fluridone, flurochloridone and flurtamone.
- HPPD (4-hydroxyphenyl-pyruvate dioxygenase) inhibitors are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.
- HPPD inhibitors include mesotrione, sulcotrione, topramezone, tembotrione, tefuryltrione, isoxachlortole, isoxaflutole, benzofenap, pyrasulfatole, pyrazolynate, pyrazoxyfen, bicyclopyrone, benzobicyclon, fenquinotrione and 5-[(2- hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)- 4(3H)-pyrimidinone (bl2a).
- HST homogentisate solenesyltransererase inhibitors
- HST inhibitors include haloxydine, pyriclor and the com ounds of Formulae A, B and C.
- HST inhibitors also include com ounds of Formulae D and E.
- R dl is H, CI or CF 3 ;
- R d2 is H, CI or Br;
- R d3 is H or CI;
- R d4 is H, CI or CF 3 ;
- R d5 is CH 3 , CH 2 CH 3 or CH 2 CHF 2 ;
- R el is H, F, CI, CH 3 or CH 2 CH 3 ;
- R e2 is H or CF 3 ;
- R e3 is H, CH 3 or CH 2 CH 3 ;
- R e4 is H, F or Br;
- R e5 is CI, CH 3 , CF 3 , OCF 3 or CH 2 CH 3 ;
- R e6 is H, CH 3 , CH 2 CHF 2 or C ⁇ CH;
- R e7 is OH,
- Cellulose biosynthesis inhibitors inhibit the biosynthesis of cellulose in certain plants. They are most effective when using a pre-aplication or early post-application on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, diclobenil, flupoxam, indaziflam, isoxaben and triaziflam.
- herbicides include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl) organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.
- mitotic disruptors e.g., flamprop-M-methyl and flamprop-M-isopropyl
- organic arsenicals e.g., DSMA, and MSMA
- 7,8-dihydropteroate synthase inhibitors e.g., chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.
- Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (bl) through (bl4) or act through a combination of modes of action listed above.
- herbicides examples include aclonifen, asulam, amitrole, clomezone, fluometuron, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dymron, methyldymron, methiozolon, ipfencarbazone, etobenzanid, fosamine, fosamine-ammonium, metam, oxaziclomefone, oleic acid, pelargonic acid and pyributicarb.
- herbicide safeners are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation.
- herbicide safeners include but are not limited to benoxacor, l-bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, 4-(dichloroacetyl)-l-oxa- 4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole,
- reaction is conducted in solvent such as 1 ,2-dimethoxyethane, 1 ,4-dioxane, toluene, tetrahydrofuran (or a mixture thereof) or t-butanol and water at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- solvent such as 1 ,2-dimethoxyethane, 1 ,4-dioxane, toluene, tetrahydrofuran (or a mixture thereof) or t-butanol and water at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- solvent such as 1 ,2-dimethoxyethane, 1 ,4-dioxane, toluene, tetrahydrofuran (or a mixture thereof) or t-butanol and water at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- Typical procedures using bromomethyl intermediates are disussed in Eur. J. Chem.2011,
- X is CI, Br or I is H or lower alkyl Q is CH 2
- Compounds of Formula Id can also be synthesized from a compound of Formula 6 by the reaction shown in Scheme 3. Hydroxymethyl derivatives of Formula 6 are reacted with a suitable organomagnesium halide in the presence of a nickel salt or complex such as nickel(II) chloride, nickel(II) bromide, nickel(II) acetoacetate or bis(tricyclohexylphosphine)nickel(II) chloride and an appropriate ligand such as tricyclohexylphosphine, l,2-bis(diphenylphosphino)ethane or l,3-bis(2,6- diisopropylphenyl)-l,3-dihydro-2H-imidazol-2-ylidene.
- a nickel salt or complex such as nickel(II) chloride, nickel(II) bromide, nickel(II) acetoacetate or bis(tricyclohexylphosphine)nickel(II) chlor
- reaction is conducted in a mixture of solvents including but not limited to dibutyl ether, diisopropyl ether and toluene at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- solvents including but not limited to dibutyl ether, diisopropyl ether and toluene
- Compounds of Formula 7 are commercially available or their preparation is known in the art.
- X is CI, Br, I or H bound to nitrogen Id
- these reactions are conducted in a solvent mixture containing tetrahydrofuran, diethyl ether or toluene at a temperature ranging from -78 °C to ambient temperature.
- Compounds of Formula 10 are commercially available or their preparation is known in the art. A typical procedure is disclosed in PCT Patent publication WO 2009/121939.
- esters of Formula 11 can be reduced to the corresponding alcohols using a wide variety of reagents, but metal hydride reagents such as lithium aluminum hydride, diisobuyl aluminum hydride or lithium borohydride are particularly general and effective. Typically, these reductions are performed in an ethereal solvent such as diethyl ether, tetrahydrofuran or 1 ,2-dimethoxyethane at temperatures ranging from -78 °C to the reflux temperature of the solvent.
- metal hydride reagents such as lithium aluminum hydride, diisobuyl aluminum hydride or lithium borohydride are particularly general and effective.
- metal hydride reagents such as lithium aluminum hydride, diisobuyl aluminum hydride or lithium borohydride are particularly general and effective.
- these reductions are performed in an ethereal solvent such as diethyl ether, tetrahydrofuran or 1 ,2-dimethoxyethane at temperatures ranging from -
- R is alkyl
- Compounds of Formula la, lb or lc can alternatively be synthesized by the reaction of N-alkoxy triazolium salts of Formula 12 with a compound of Formula 13 in the presence of a base as shown in Scheme 7.
- the counterion is typically a non-nucleophilic anion such as tetrafluoroborane or trifluoromethanesufonate.
- Appropriate solvents for these substitution reactions include acetonitrile, methanol and tetrahydrofuran either alone or mixtures thereof. These reactions are usually conducted at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- Bases such as potassium carbonate, sodium hydride, sodium carbonate, potassium tert-butoxide, and many others can be employed.
- R lower alkyl
- Compounds of Formula la, lb or lc can also be synthesized from a compound of Formula 14 by the reaction shown in Scheme 8 of an electron-deficient aromatic or heteroaromatic compound of Formula 15 wherein X is a suitable leaving group, for example, a halogen, sulfonyl (such as alkylsulfonyl, trifluoromethanesulfonyl, phenylsulfonyl or /?-toluenesulfonyl) or lower alkoxide, in the presence of an appropriate base such as potassium carbonate, cesium carbonate or potassium hydroxide.
- X is a suitable leaving group, for example, a halogen, sulfonyl (such as alkylsulfonyl, trifluoromethanesulfonyl, phenylsulfonyl or /?-toluenesulfonyl) or lower alkoxide, in the presence of an appropriate base
- reaction is conducted in a solvent such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone or acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- solvent such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone or acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- solvent such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone or acetonitrile
- a suitable nitro-containing aromatic or heteroaromatic compound of Formula 16 can be used to enhance the reaction rate. It is obvious to one skilled in the art that reduction of the nitro group followed by diazotization/reduction of the resulting aniline will satisfactorily remove the activating nitro group. A typical procedure for this series of steps is disclosed in Angew. Chem., Int. Ed. 2010, 49(11), 2018-2022. Compounds of Formulae 15 and 16 are commercially available or their preparation is known in the art.
- a compound of Formula 2a can be synthesized by the reaction of triazole N-oxides of Formula 17 with a suitable activator such as an acid halide, acid anhydride or silyl halide followed by acidic or basic hydrolysis.
- a suitable activator such as an acid halide, acid anhydride or silyl halide followed by acidic or basic hydrolysis.
- the activator is selected from acetyl chloride, acetic anhydride (which can also act as the solvent) or trimethylsilyl iodide.
- Other solvents appropriate for this reaction include chloroform and dichloromethane. These reactions are usually conducted at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- Basic hydrolysis is typically conducted with a base such as sodium hydroxide, potassium hydroxide or potassium carbonate in a solvent such as water, methanol, ethanol or a mixture tetrahydrofuran and water at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- Acidic hydrolysis is typically conducted with, but not limited to, an acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or acetic acid in a solvent such as chloroform, toluene, methanol, ethanol or water (or a mixture of said solvents) at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- a typical procedure using acetyl chloride as the activator followed by basic hydrolysis is disclosed in Bull. Chim. Belg. 1997, 106(11), 717-728.
- a typical procedure using trimethylsilyl iodide as the activator followed by acidic hydrolysis is discussed Chem. Scan. 1996, 50(6), 549-
- a compound of Formula 4 is a particularly useful intermediate for use in the preparation of a compound of Formula 1 and can be prepared from several different precursors.
- esters of Formula 18 can be converted to alcohols of Formula 6.
- Alcohols of Formula 6 can then be converted to the compounds of Formula 4 using a wide range of reagents such as thionyl chloride, phosphorus trichloride, phosphorus tribromide, triphenylphosphine/bromine, triphenylphosphine/iodine.
- halogenation methods using hydrohalides in solvents such as acetic acid, acetonitrile, diethyl ether, tetrahydrofuran, dichloromethane, water or a mixture of water with the aforementioned solvents, at temperatures ranging from 0 °C to the reflux temperature of the solvent can be used.
- solvents such as acetic acid, acetonitrile, diethyl ether, tetrahydrofuran, dichloromethane, water or a mixture of water with the aforementioned solvents
- solvents such as acetic acid, acetonitrile, diethyl ether, tetrahydrofuran, dichloromethane, water or a mixture of water with the aforementioned solvents
- solvents such as acetic acid, acetonitrile, diethyl ether, tetrahydrofuran, dichloromethane, water or a mixture of water with the aforementioned solvents
- R is lower atkyl
- a compound of Formula 4 can be prepared from triazole N-oxides of Formula 19 by the one-step procedure shown in Scheme 11. Reaction of a compound of Formula 19 with halogenating agent such as phosphorus oxybromide or phosphorus oxychloride, in solvents such as 1,4-dioxane, 1 ,2-dichloroethane, chloroform or toluene, at temperatures ranging from ambient to the reflux temperature of the solvent affords compounds of Formula 4 directly.
- halogenating agent such as phosphorus oxybromide or phosphorus oxychloride
- bromides of Formula 4 can also be prepared by radical bromination of a compound of Formula 20 using a brominating agent such as N-bromosuccinimide or bromine, a radical initiator such as azobisisobutyronitrile, benzoyl peroxide or a UV light source, in solvents such as carbon tetrachloride or trifluoromethylcyclohexane at temperatures ranging from ambient to the reflux temperature of the solvent.
- a brominating agent such as N-bromosuccinimide or bromine
- a radical initiator such as azobisisobutyronitrile, benzoyl peroxide or a UV light source
- solvents such as carbon tetrachloride or trifluoromethylcyclohexane
- triazoles of Formula 21 can be converted into N-aryl triazoles of Formula 11a which are useful for preparing alcohols of Formula If as depicted in Scheme 6.
- Compounds of Formulae 15 (where R is lower alkyl) and 16 are commercially available or their preparation is known in the art.
- Compounds of Formula 18 can be prepared as shown in Scheme 14. Reaction of a dicarbonyl compound of Formula 22 with a diazonium salt in the presence of an acid acceptor results in a coupling reaction to form a compound of Formula 23.
- Suitable solvents include lower carboxylic acids such as acetic acid, lower alcohols such as methanol or ethanol, water, and mixtures thereof. Acid acceptors such as, but not limited to, alkali carbonates, bicarbonates, phosphates and acetates can be employed in this reaction.
- Compounds of Formula 23 can be cyclized to compounds of Formula 18 by reaction with an ammonium salt in the presence of an oxidizing agent. Suitable ammonium salts include halides, acetate, and sulfate among others.
- the oxidizing agent is preferably, but not limited to, a Cu(II) salt such as copper(II) sulfate, copper(II) chloride or copper(II) bromide or N-iodosuccinimide. Typical conditions for this procedure are described in U.S. Patent Application 20060014785. Scheme 14
- Compounds of Formula lib can be prepared as shown in Scheme 15.
- the coupling reaction of a dicarbonyl compound of Formula 24 with a diazonium salt in the presence of an acid acceptor can form a compound of Formula 25.
- Suitable solvents include lower carboxylic acids such as acetic acid, lower alcohols such as methanol or ethanol, water, and mixtures thereof. Acid acceptors such as, but not limited to, alkali carbonates, bicarbonates, phosphates and acetates can be employed in this reaction.
- Compounds of Formula 25 can be cyclized to compounds of Formula lib by reaction with an ammonium salt in the presence of an oxidizing agent. Suitable ammonium salts include halides, acetate, and sulfate among others.
- the oxidizing agent is preferably, but not limited to, a Cu(II) salt such as copper(II) sulfate, copper(II) chloride or copper(II) bromide or N-iodosuccinimide. Typical conditions for this procedure are described in U.S. Patent Application 20060014785.
- compounds of Formula 12 can be synthesized by the reaction of triazole N-oxides of Formula 17 with strong alkylating reagents such as trimethyloxonium tetrafluoroborate or methyl trifluoromethanesulfonate.
- Preferred solvents for this substitution reaction include dichloromethane, chloroform and 1,2-dichloroethane. The reactions are usually conducted at temperatures ranging from 0 °C to the reflux temperature of the solvent. Typical procedures are disclosed in J. Chem. Soc, Perkin Transactions 1 1982, 2749-2756 and references cited therein.
- R lower alkyl or benzyl
- a compound of Formula 21 can be obtained by removal of an appropriate protecting group such as a trialkylsilyl group, (i.e. trimethylsilyl), or an optionally substituted benzyl group (i.e. benzyl or /?-methoxybenzyl) from compounds of Formula 26.
- the /?-methoxybenzyl group is of particular value as an intermediate to prepare a compound of Formula 1 via a compound of Formula 4 as shown in Scheme 2.
- Deprotection of a compound of Formula 26 wherein PG is /?-methoxybenzyl is typically performed via one of the following two methods.
- acid-catalyzed deprotection is usually conducted in neat trifluoroacetic acid or as a mixture with a solvent such as dichloromethane or 1,2-dichloroethane at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- a solvent such as dichloromethane or 1,2-dichloroethane
- a typical procedure is disclosed in PCT Patent publication WO 2005/073192.
- the /?-methoxybenzyl group can be removed using an oxidant such as eerie ammonium nitrate or 2,3-dichloro-5,6-dicyano-l,4-benzoquinone in a mixture of acetonitrile and water or a mixture of dichloromethane and water, respectively.
- the useful temperature range for these reactions is from ambient to the reflux temperature of the solvent.
- a typical procedure is disclosed in PCT Patent Publication WO 2007/071900.
- PG is a protecting group
- a compound of Formula 23 can be prepared from a compound of Formula 27 using reaction conditions similar to those discussed in the method of Scheme 16.
- R 1 is either a lower alkoxy group or a haloalkoxy group
- Scheme 18 For an exemplary preparation of a compound of Formula 27 wherein R 1 is either a lower alkoxy group or a haloalkoxy group, see PCT Patent Publication WO 2007/096576.
- R is lower alkyl
- R is lower alkyl
- a compound of Formula 19a wherein R 1 can independently be H or C 1 -C4 alkyl can be synthesized by the reaction of a compound of Formula 28 with a suitable oxidant as shown in Scheme 19.
- Suitable oxidants include a Cu(II) salt, such as copper(II) sulfate, copper(II) chloride or copper(II) bromide, or N-iodosuccinimide.
- the preferred solvents for the reaction are pyridine, carbon tetrachloride, methanol, ethanol, water and aqueous mixtures of the aforementioned solvents.
- the reactions are usually conducted at temperatures ranging from 0 °C to the reflux temperature of the solvent. A typical procedure is disclosed in J. Chem. Soc, Perkin Transactions 1 1981, 503-513.
- Compounds of Formula 28 are commercially available or their preparation is known in the art.
- R 1 is H or d-C 4 alkyl
- a compound of Formula 17a wherein R 1 is H or C1 -C4 alkyl can be synthesized by the reaction of a compound of Formula 29 with a suitable oxidant as shown in Scheme 20.
- Suitable oxidants and solvents include those discussed for Scheme 19.
- the reactions are usually conducted at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- a typical procedure is disclosed in J. Chem. Soc, Perkin Transactions 1 1981, 503-513.
- Compounds of Formula 29 are commercially available or their preparation is known in the art. A typical procedure is disclosed in J. Chem. Soc, Perkin Transactions 1 1981, 503-513.
- Scheme 20
- R 1 is H or C r C 4 alkyl
- a compound of Formula 26a can be synthesized by the reaction of triazoles of Formula 30 with a wide range of carbon, oxygen, sulfur and nitrogen nucleophiles including cyanide, dialkyl malonates, aryl acetonitriles, aryl acetic acids, aryl acetic esters, amines, phenols, alcohols, thiophenols, alkyl thiols and anilines, optionally in the presence of a base, as shown in Scheme 21.
- Typical bases including sodium hydride, sodium methoxide, sodium ethoxide, cesium carbonate, potassium carbonate or potassium tert-butoxide can be employed.
- Solvents suitable for this substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols and acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- Solvents suitable for this substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols and acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- R lower alkyl
- R lower alkyl
- PG is a protecting group
- Q is O or S
- a compound of Formula 27a can be synthesized by the reaction of triazoles of Formula 31 with a wide range of carbon, nitrogen, oxygen and sulfur nucleophiles including cyanide, dialkyl malonates, aryl acetonitriles, aryl acetic acids, aryl acetic esters, amines, phenols, alcohols, thiophenols, alkyl thiols and anilines, optionally in the presence of a base, as shown in Scheme 22.
- Typical bases including sodium hydride, sodium methoxide, sodium ethoxide, cesium carbonate, potassium carbonate or potassium tert- butoxide can be employed.
- Solvents suitable for this substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols and acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- Solvents suitable for this substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols and acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent.
- PG is /?-methoxybenzyl Q is O or S
- the preferred solvents for the substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols, acetonitrile and water or a mixture thereof at temperatures ranging from 0 °C to the reflux temperature of the solvent.
- a typical procedure is disclosed in J. Org. Chem. 2008, 75(11), 4317-4319.
- a compound of Formula 30 is commercially available or its preparation is known in the art.
- Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M+l) formed by addition of H + (molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP + ) where "amu” stands for atomic mass units. The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g., 37 C1, 81 Br) is not reported.
- Step A Preparation of 4-Methyl-2-[4-(trifluoromethyl)phenyl]-2H- 1,2, 3-triazole 1- oxide
- Step B Preparation of l-Methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H- 1,2,3- triazolium tetrafluoroborate (1 : 1)
- Step C Preparation of 4-methoxy-5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-l,2,3- triazole Sodium metal (0.25 g, 1 1.0 mmol) was stirred at 23 °C in methanol (10 mL) until a clear solution was obtained. This sodium methoxide solution was added to crude l-methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-l ,2,3-triazolium tetrafluoroborate (1 : 1) (i.e. the product of Step B, 1.1 g, 3.2 mmol). The reaction mixture was stirred at 23 °C for 6 h, during which time a white precipitate formed.
- the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (40 mL, 10 mL). The organic layer was dried (MgSC"4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to afford the title compound (0.82 g) as a colorless solid.
- Step D Preparation of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-
- Step E Preparation of 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-l ,2,3-triazol- 4-yl]methyl]-2-(trifluoromethyl)pyridine
- the mixture was heated to reflux and stirred for 17 h.
- the reaction mixture was diluted with water (20 mL) and extracted twice with ethyl acetate (25 mL, 15 mL).
- the organic layer was dried (MgS0 4 ) and concentrated under reduced pressure.
- the crude residue was purified by chromatography on silica gel eluting with 10%> ethyl acetate in hexanes to afford the title compound (0.12 g) as a pale yellow solid.
- Step A Preparation of 4-methoxy-2-[4-(trifluoromethyl)phenyl]-5-[[3- (trifluoromethyl)- lH-pyrazol- 1 -yl]methyl]-2H- 1 ,2,3-triazole
- the reaction mixture was diluted with water (20 mL) and extracted with diethyl ether (2 x 25 mL). The organic layer was dried (MgS0 4 ) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 5% ethyl acetate in hexanes to afford the title compound (0.105 g) as a colorless solid.
- Step A Preparation of 2-(4-fluorophenyl)-4-methyl-2H-l,2,3-triazole 1-oxide
- 4-fluorophenylhydrazine hydrochloride 5.85 g, 36 mmol
- the reaction mixture was stirred at 23 °C for 16 h, and then concentrated under reduced pressure.
- the crude residue was dissolved in pyridine (120 mL).
- a solution of copper(II) sulfate pentahydrate (18 g, 72 mmol) in water (55 mL) was added dropwise over 4 min.
- Step B Preparation of 2-(4-fluorophenyl)-5-methyl-2H-l ,2,3-triazol-4-yl acetate
- Step C Preparation of 2-(4-fluorophenyl)-2,3-dihydro-5-methyl-4H- 1 ,2,3-triazol-4- one
- the organic layer was washed successively with water and saturated aqueous sodium chloride solution, dried (MgS0 4 ), filtered, and concentrated under reduced pressure.
- the crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (4.2 g) as a viscous light yellow oil that solidified upon standing to form an off- white solid.
- Step A Preparation of l-(azidomethyl)-4-methoxybenzene
- Step B Preparation of ethyl 5-hydroxy-l-[(4-methoxyphenyl)methyl]-lH- 1,2,3- triazole-4-carboxylate
- Step C Preparation of ethyl 5-chloro-l-[(4-methoxyphenyl)methyl]-lH- 1,2,3- triazole-4-carboxylate
- Step D Preparation of ethyl- l-[(4-methoxyphenyl)methyl]-5-(3- (trifluoromethoxy)phenoxy]-lH-l,2,3-triazole-4-carboxylate
- Step E Preparation of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2H-l,2,3-triazole-4- carboxylate
- a solution of ethyl- l-[(4-methoxyphenyl)methyl]-5-(3-(trifluoromethoxy)phenoxy]- lH-l,2,3-triazole-4-carboxylate (i.e. the product of Step D, 1.50 g, 3.4 mmol) in trifluoroacetic acid (35 mL) was heated to 65 °C with stirring for 5 h. The reaction mixture was concentrated to dryness under reduced pressure.
- Step F Preparation of ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-
- the organic layer was dried (MgS0 4 ) and concentrated under reduced pressure to afford the crude product.
- the crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (0.76 g) as a pale yellow oil.
- Step G Preparation of 2-(2-amino-4-trifluoromethyl-phenyl)-5-(3-trifluoromethoxy- phenoxy)-2H-[l,2,3]triazole-4-carboxylic acid ethyl ester
- the reaction mixture was stirred at -20 °C for 1 h, after which an aqueous solution of hypophosphorus acid (3.9 g, 29.4 mmol, 50% in water) was added. The solution was stirred at 23 °C for 14 h. The reaction mixture was diluted with saturated aqueous sodium chloride solution (20 mL), extracted with ethyl acetate (2 x 40 mL), and washed with saturated aqueous sodium bicarbonate solution (2 x 20 mL).
- Step I Preparation of 5 - [3 -(trifluoromethoxy)phenoxy] -2- [4-
- Step A Preparation of 4-(Bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4- (trifluoromethyl)phenyl)-2H- 1 ,2,3-triazole
- the reaction mixture was diluted with water (20 mL), extracted with ethyl acetate (3 x 15 mL), and washed with saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was dried (MgSC" 4 ) and concentrated under reduced pressure to obtain the title compound (0.19 g) as a pale yellow solid. The title compound was used directly in the next step without further purification.
- a reaction vial was charged with a magnetic stir bar, 4-(bromomethyl)-5-[3- (trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl)-2H-l,2,3-triazole (i.e. the product of Step A, 0.075 g, 0.16 mmol) and palladium on carbon (5 weight%>, 0.033 g, 0.03 mmol).
- the vial was purged with nitrogen gas, and then absolute ethanol (5 mL) was added.
- the vial was purged and backfilled with hydrogen gas 10 times.
- the solution was stirred at 23 °C for 6 h under a balloon of hydrogen gas.
- reaction mixture was quenched with triethylamine (0.1 mL), stirred for 5 min., filtered, and concentrated under reduced pressure.
- the residue was diluted with water (5 mL) and extracted with ethyl acetate (2 x 5 mL). The organic layer was dried (MgS0 4 ) and concentrated under reduced pressure to obtain the title compound (0.046 g,) as a beige solid.
- Step A Preparation of 4-ethyl-5-[3-(trifluoromethoxy)phenoxy]-2-[4-
- Step B Preparation of [2-(2,4-difluoro-phenyl)-5-methyl-2H-[l,2,3]triazol-4-yl]- methanol
- Step C Preparation of 4-(bromomethyl)-2-(2,4-difluorophenyl)-5-methyl-2H-l,2,3- triazole
- Step D Preparation of 4-[[2-(2,4-difluorophenyl)-5-methyl-2H-l,2,3-triazol-4- yl]methyl]-2-(trifluoromethyl)pyridine
- the reaction mixture was diluted with water and extracted with ethyl acetate.
- the organic layer was dried (MgS0 4 ) and concentrated under reduced pressure.
- the crude residue was purified by twice by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes, and then was purified by reverse-phase chromatography on C 18 silica gel to afford the title compound (0.18 g) as a colorless solid.
- Step A Preparation of ethyl 5-ethoxy-2-(4-fluorophenyl)-2H-l,2,3-triazole-4- carboxylate
- the suspension was stirred at 23 °C for 30 min., and then the solid was filtered and washed with water (40 mL).
- the still wet hydrazone was dissolved in pyridine (150 mL).
- a solution of copper (II) sulfate (49.7 g, 199 mmol) in water (150 mL) was added at once.
- the dark mixture was heated to 90 °C for 4 h.
- the majority of the pyridine (-100 mL) was removed under vacuum.
- the residue was diluted with ethyl acetate (200 mL), water (100 mL) and 2 M sulfuric acid (80 mL).
- the resulting emulsion was filtered through Celite® diatomaceaous earth filter aid.
- Step B Preparation of 5-ethoxy-2-(4-fluorophenyl)-N-methoxy-N-methyl-2H- 1,2,3- triazole-4-carboxamide
- reaction mixture was cooled to 0 °C and carefully quenched by the dropwise addition of water (2 mL).
- Dichloromethane, (50 mL), sodium sulfate and water (3 mL) were added sequentially to the mixture which was then stirred for 20 min. at 23 °C.
- the mixture was dried (Na 2 S0 4 and MgS0 4 ) and concentrated under reduced pressure to obtain the title compound (3.7 g) as an orange solid.
- Step C Preparation of [5-ethoxy-2-(4-fluorophenyl)-2H-l,2,3-triazol-4-yl][2-
- Step D Preparation of 4-[[5-ethoxy-2-(4-fluorophenyl)-2H-l,2,3-triazol-4-yl]methyl]-
- the reaction mixture was cooled to 23 °C and neutralized to ⁇ pH 7 with 1 M NaOH and a saturated aqueous sodium bicarbonate solution.
- the mixture was extracted with ethyl acetate (2 x 15 mL), dried (MgSC ⁇ ) and concentrated under reduced pressure.
- the crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (2.1 g) as an off- white solid.
- n means normal, i means iso, Me means methyl, Et means ethyl, Pr means propyl, z ' -Pr means isopropyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy and SMe means methylthio.
- J-1A, J-2A, J-10A, J-17A, J-17B, J-18A, J-18B, J-20A, J-22A and J-29A refer to the following structures:
- J is J-2A; Q is O; R 1 is Me; and A is
- Table 2 is constructed in the same manner except that the Row Heading "J is J-2A; Q is O, R 1 is Me; and A is” is replaced with the Row Heading listed for Table 2 below (i.e. "J is J-2A; Q is O; R1 is Et; and A is”). Therefore the first entry in Table 2 is a compound of Formula 1 wherein R 1 is Et; Q is O; A is Ph(4-F) (i.e. 4-fluorophenyl); and J is J-2A. Tables 3 through 125 are constructed similarly.
- J J-2A; Q is O; R 1 is CH 2 OCH 3 ; and A is
- J is J-2A; Q is O; R 1 is OCH 2 CF 3 ; and A is
- J is J-2A; Q is CH 2 ; R 1 is Me; and A is
- J is J-2A; Q is CH 2 ; R 1 is Et; and A is
- J is J-2A; Q is CH 2 ; R 1 is «-Pr; and A is
- J is J-2A; Q is CH 2 ; R 1 is z ' -Pr; and A is
- J is J-2A; Q is CH 2 ; R 1 is OMe; and A is
- J is J-2A; Q is CH 2 ; R 1 is SMe; and A is
- J is J-2A; Q is CH 2 ; R 1 is OCHF 2 ; and A is
- J is J-2A; Q is CH 2 ; R 1 is OEt; and A is
- J is J-2A;
- Q is CH 2 ;
- R 1 is OCH 2 CF 3 ; and
- A is
- J J-IA
- Q is O
- R 1 is «-Pr
- A is
- J is J-IA; Q is O; R 1 is OCHF2; and A is
- 29 J is J-IA; Q is O; R 1 is OEt; and A is
- J is J-IA; Q is O; R 1 is OCH 2 CF 3 ; and A is
- J is J-IA; Q is CH 2 ; R 1 is Et; and A is
- J is J-IA; Q is CH 2 ; R 1 is n-Pr; and A is
- J is J-IA; Q is CH 2 ; R 1 is SMe; and A is
- J is J-IA; Q is CH 2 ; R 1 is CH 2 OCH 3 ; and A is
- J is J-IA; Q is CH 2 ; R 1 is OEt; and A is
- J is J-IOA; Q is O; R 1 is OMe; and A is
- J is J-10A; Q is CH 2 ; R 1 is Me; and A is
- J is J-IOA
- Q is CH 2
- R 1 is OMe
- A is
- J is J-IOA
- Q is CH 2
- R 1 is OCHF 2
- A is
- J is J-29A; Q is O; R 1 is OCHF 2 ; and A is
- 56 J is J-29A; Q is CH 2 ; R 1 is OCHF 2 ; and A is
- J-IA J-IA
- R 1 is OMe
- A is
- J-IA J-IA
- Q is S
- R 1 is Me
- A is
- J-IA J-IA
- Q is S
- R 1 is OMe
- A is
- J J-IA
- Q is S
- R 1 is OCHF 2
- A is
- 77 J is J-IA; Q is NH; R 1 is Me; and A is
- 87 J is J-1A; Q is CHF; R 1 is OMe; and A is
- 96 J is J-22A; Q is CH 2 ; R 1 is OCHF 2 ; and A is
- J-1A 99 J is J-1A; Q is O; R 1 is Br; and A is
- 101 J is J-18A; Q is CH 2 ; R 1 is Et; and A is
- 104 J is J-18A; Q is CH 2 ; R 1 is OCHF 2 ; and A is
- 105 J is J-18A; Q is CH 2 ; R 1 is CI; and A is
- 106 J is J-20A; Q is CH 2 ; R 1 is Et; and A is
- 107 J is J-20A; Q is CH 2 ; R 1 is Me; and A is
- 109 J is J-20A; Q is CH 2 ; R 1 is OCHF 2 ; and A is
- 112 J is J-17A; Q is CH 2 ; R 1 is Me; and A is
- 115 J is J-17A; Q is CH 2 ; R 1 is CI; and A is 116 J is J-17B; Q is CH 2 ; 1 is Et; and A is
- 117 J is J-17B; Q is CH 2 ; R 1 is Me; and A is
- 118 J is J-17B; Q is CH 2 ; R 1 is OMe; and A is
- 121 J is J-18B; Q is CH 2 ; R 1 is Et; and A is
- 122 J is J-18B; Q is CH 2 ; R 1 is Me; and A is
- 124 J is J-18B; Q is CH 2 ; R 1 is OCHF 2 ; and A is
- 125 J is J-18B; Q is C3 ⁇ 4; R 1 is CI; and A is
- a compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
- a composition i.e. formulation
- additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
- the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
- Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels.
- aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion.
- nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
- compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment.
- Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
- An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
- Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
- the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
- Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
- Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
- Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy- 4-methyl-2-pentan
- Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof.
- plant seed and fruit oils e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
- animal-sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
- Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
- alkylated fatty acids e.g., methylated, ethylated, butylated
- Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
- the solid and liquid compositions of the present invention often include one or more surfactants.
- surfactants also known as “surface-active agents”
- surface-active agents generally modify, most often reduce, the surface tension of the liquid.
- surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
- Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene
- Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
- Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
- amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amine
- Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon 's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
- compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
- formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes.
- Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
- formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
- the compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent.
- Solutions, including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water.
- Active ingredient slurries, with particle diameters of up to 2,000 ⁇ can be wet milled using media mills to obtain particles with average diameters below 3 ⁇ .
- Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 um range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques.
- Pellets can be prepared as described in U.S. 4,172,714.
- Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
- Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
- Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
- Compound 14 65.0% dodecylphenol polyethylene glycol ether 2.0%> sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%
- Compound 15 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)
- Compound 16 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0%> sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%
- the compounds of the mention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil).
- postemergence weed control i.e. applied after weed seedlings emerge from the soil
- preemergence weed control i.e. applied before weed seedlings emerge from the soil.
- Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures.
- Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
- important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa
- Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.
- the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth
- the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
- a herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
- Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
- Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes.
- the present invention also pertains to a composition
- a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent.
- the other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent.
- one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
- a mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilana
- herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
- bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
- Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
- plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl
- plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-
- the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1 :3000 and about 3000: 1. Of note are weight ratios between about 1 :300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1).
- weight ratios between about 1 :300 and about 300: 1 for example ratios between about 1 :30 and about 30: 1).
- One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.
- combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable.
- synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.
- safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
- a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
- herbicide safeners such as allidochlor, N-(aminocarbonyl)-2-methylbenzenesulfonamide, benoxacor, BCS (1- bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, cyprosulfonamide, dichlormid, 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), dicyclonon, dietholate, ethyl l,6-dihydro-l-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, fenchlorazole- ethyl, fenclorim, flurazole, flux
- herbicide safeners such as allidoch
- Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
- composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- Preferred for better control of undesired vegetation e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety
- a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention.
- Compound 1 in the Component (a) column is identified in Index Table A.
- the second column of Table Al lists the specific Component (b) compound (e.g., "2,4-D" in the first line).
- the third, fourth and fifth columns of Table Al lists ranges of weight ratios for rates at which the Component (a) compound is typically applied to a field-grown crop relative to Component (b) (i.e. (a):(b)).
- the first line of Table Al specifically discloses the combination of Component (a) (i.e. Compound 1 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1 : 192 to 6: 1.
- the remaining lines of Table Al are to be construed similarly.
- Component (a) Component (b) Weiaht Ratio Weiaht Ratio Weiaht Ratio Weiaht Ratio
- Component (a) Component (b) Weiaht Ratio Weiaht Ratio Weiaht Ratio Weiaht Ratio
- Component (a) Component (b) Weiaht Ratio Weiaht Ratio Weiaht Ratio Weiaht Ratio
- Component (a) Component (b) Weiaht Ratio Weiaht Ratio Weiaht Ratio Weiaht Ratio
- Component (a) Component (b) Weiaht Ratio Weiaht Ratio Weiaht Ratio Weiaht Ratio
- Component (a) Component (b) Weiaht Ratio Weiaht Ratio Weiaht Ratio Weiaht Ratio
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261719166P | 2012-10-26 | 2012-10-26 | |
PCT/US2013/065663 WO2014066164A1 (en) | 2012-10-26 | 2013-10-18 | Substituted triazoles as herbicides |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2912022A1 true EP2912022A1 (en) | 2015-09-02 |
EP2912022B1 EP2912022B1 (en) | 2016-11-23 |
Family
ID=49546616
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13786569.7A Active EP2912022B1 (en) | 2012-10-26 | 2013-10-18 | Substituted triazoles as herbicides |
Country Status (16)
Country | Link |
---|---|
US (1) | US9302999B2 (en) |
EP (1) | EP2912022B1 (en) |
JP (1) | JP2016503396A (en) |
CN (1) | CN104755467A (en) |
AR (1) | AR093117A1 (en) |
AU (1) | AU2013335001B2 (en) |
BR (1) | BR112015009326B8 (en) |
CA (1) | CA2887625A1 (en) |
CL (1) | CL2015001066A1 (en) |
EA (1) | EA028671B1 (en) |
IL (1) | IL238029A0 (en) |
MX (1) | MX2015005268A (en) |
TN (1) | TN2015000108A1 (en) |
TW (1) | TW201418242A (en) |
UY (1) | UY35099A (en) |
WO (1) | WO2014066164A1 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10202361B2 (en) | 2014-08-29 | 2019-02-12 | Fmc Corporation | Pyridazinones as herbicides |
WO2016033285A1 (en) | 2014-08-29 | 2016-03-03 | E. I. Du Pont De Nemours And Company | Herbicidal triazoles |
CN109867632B (en) * | 2017-12-01 | 2021-06-01 | 中国科学院大连化学物理研究所 | 1,2, 3-triazole derivative and synthesis and application thereof |
CA3086401A1 (en) * | 2017-12-29 | 2019-07-04 | Biomarin Pharmaceutical Inc. | Glycolate oxidase inhibitors for the treatment of disease |
CN109535092B (en) * | 2018-12-24 | 2021-05-11 | 温州大学 | Preparation method of benzotriazole derivatives |
JP2022536969A (en) * | 2019-06-19 | 2022-08-22 | ビオマリン プハルマセウトイカル インコーポレイテッド | Glycolate oxidase inhibitors for the treatment of diseases |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
CH444873A (en) * | 1963-04-11 | 1967-10-15 | Isis Chemie Kg | Process for the preparation of vicinal triazoles |
DE1226591B (en) * | 1963-11-12 | 1966-10-13 | Isis Chemie K G | Process for the preparation of vicinal triazoles |
US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
DE3246493A1 (en) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING WATER-DISPERSIBLE GRANULES |
GB8429307D0 (en) * | 1984-11-20 | 1984-12-27 | Shell Int Research | Heterocyclic herbicides |
CN1035326C (en) * | 1985-07-15 | 1997-07-02 | 赫彻斯特股份公司 | Process for preparing derivates of 1,2,4-triazols |
US4610717A (en) * | 1985-11-26 | 1986-09-09 | Shell Oil Company | Certain 5-(R-oxy)-1-phenyl or (3-(trifluoromethyl)phenyl)triazoles, useful for controlling undesired plant growth |
GB2193493A (en) | 1986-08-06 | 1988-02-10 | Shell Int Research | Herbicidal triazoles and tetrazoles |
US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
EP0350237A3 (en) * | 1988-07-08 | 1990-08-29 | Schering Agrochemicals Limited | Triazole insecticides |
YU47834B (en) * | 1989-08-10 | 1996-01-09 | Schering Agrochemical Limited | THE AZOLE PESTICIDE |
ES2126553T3 (en) | 1989-08-30 | 1999-04-01 | Aeci Ltd | DOSING DEVICE AND ITS USE. |
HU210697B (en) | 1990-03-12 | 1995-06-28 | Du Pont | Water-dispersible or water-soluble pesticide granular composition containing heat-activated binders |
DE69122201T2 (en) | 1990-10-11 | 1997-02-06 | Sumitomo Chemical Co | Pesticides composition |
JPH0649041A (en) * | 1992-07-28 | 1994-02-22 | Mitsubishi Petrochem Co Ltd | Carbamoyltriazole derivative, herbicide with the same as active ingredient and production of the same derivative |
TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
SE0400208D0 (en) | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
CA2567437A1 (en) | 2004-05-25 | 2005-12-08 | Metabolex, Inc. | Substituted triazoles as modulators of ppar and methods of their preparation |
JP2008500358A (en) | 2004-05-25 | 2008-01-10 | メタボレックス インコーポレーティッド | Bicyclic substituted triazoles as modulators of PPARs and methods for their preparation |
GB0526044D0 (en) | 2005-12-21 | 2006-02-01 | Syngenta Ltd | Novel herbicides |
AR058408A1 (en) | 2006-01-02 | 2008-01-30 | Basf Ag | PIPERAZINE COMPOUNDS WITH HERBICITY ACTION |
GB0603891D0 (en) | 2006-02-27 | 2006-04-05 | Syngenta Ltd | Novel herbicides |
FR2929615B1 (en) | 2008-04-02 | 2010-12-17 | Tfchem | C-ARYL GLYCOSIDE COMPOUNDS FOR THE TREATMENT OF DIABETES AND OBESITY |
CN101302217B (en) * | 2008-07-02 | 2010-12-22 | 南开大学 | Triazole compounds, preparation and use thereof |
US20100069644A1 (en) * | 2008-09-15 | 2010-03-18 | Xiaodong Shi | Method of regio-selective synthesis of tri-substituted-1, 2, 3-triazoles |
CA2803118C (en) | 2010-07-09 | 2015-11-03 | Pfizer Limited | Sulfonamide derivatives as nav 1.7 inhibitors |
-
2013
- 2013-10-09 TW TW102136472A patent/TW201418242A/en unknown
- 2013-10-18 CA CA2887625A patent/CA2887625A1/en not_active Abandoned
- 2013-10-18 CN CN201380054856.0A patent/CN104755467A/en active Pending
- 2013-10-18 EA EA201590818A patent/EA028671B1/en unknown
- 2013-10-18 JP JP2015539675A patent/JP2016503396A/en active Pending
- 2013-10-18 WO PCT/US2013/065663 patent/WO2014066164A1/en active Application Filing
- 2013-10-18 AU AU2013335001A patent/AU2013335001B2/en active Active
- 2013-10-18 EP EP13786569.7A patent/EP2912022B1/en active Active
- 2013-10-18 US US14/437,360 patent/US9302999B2/en active Active
- 2013-10-18 BR BR112015009326A patent/BR112015009326B8/en active IP Right Grant
- 2013-10-18 MX MX2015005268A patent/MX2015005268A/en unknown
- 2013-10-24 AR ARP130103857A patent/AR093117A1/en active IP Right Grant
- 2013-10-25 UY UY0001035099A patent/UY35099A/en not_active Application Discontinuation
-
2015
- 2015-03-23 TN TNP2015000108A patent/TN2015000108A1/en unknown
- 2015-03-30 IL IL238029A patent/IL238029A0/en unknown
- 2015-04-24 CL CL2015001066A patent/CL2015001066A1/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO2014066164A1 * |
Also Published As
Publication number | Publication date |
---|---|
BR112015009326A2 (en) | 2017-10-03 |
EP2912022B1 (en) | 2016-11-23 |
JP2016503396A (en) | 2016-02-04 |
US9302999B2 (en) | 2016-04-05 |
BR112015009326B8 (en) | 2019-12-17 |
TN2015000108A1 (en) | 2016-06-29 |
EA201590818A1 (en) | 2016-03-31 |
US20150284343A1 (en) | 2015-10-08 |
WO2014066164A1 (en) | 2014-05-01 |
UY35099A (en) | 2014-05-30 |
TW201418242A (en) | 2014-05-16 |
MX2015005268A (en) | 2015-08-14 |
CL2015001066A1 (en) | 2015-10-02 |
AU2013335001B2 (en) | 2018-03-08 |
IL238029A0 (en) | 2015-05-31 |
BR112015009326B1 (en) | 2019-10-22 |
AR093117A1 (en) | 2015-05-20 |
EA028671B1 (en) | 2017-12-29 |
CN104755467A (en) | 2015-07-01 |
CA2887625A1 (en) | 2014-05-01 |
AU2013335001A1 (en) | 2015-04-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2934891C (en) | Pyrimidinyloxy benzene derivatives as herbicides | |
CA2932433C (en) | Herbicidal substituted pyrimidinyloxy benzene compounds | |
EP3137456B1 (en) | Pyridazinone herbicides | |
EP3271350B1 (en) | Substituted pyrimidinyloxy pyridine derivatives as herbicides | |
EP3601263B1 (en) | Novel pyridazinone herbicides | |
EP3169676A1 (en) | Bis(aryl)catechol derivatives as herbicides | |
AU2013335001B2 (en) | Substituted triazoles as herbicides | |
AU2018262478B2 (en) | Pyrimidinyloxy benzo-fused compounds as herbicides | |
EP3185684A1 (en) | Herbicidal triazoles | |
WO2015167795A1 (en) | Herbicidal substituted 3-phenyl-4-fluorobenzoyl pyrazoles | |
US20150105252A1 (en) | Substituted pyrazoles as herbicides | |
WO2024072768A1 (en) | Substituted fluoropyridine as herbicides | |
WO2023129493A1 (en) | Substituted cyclopropylpyrimidne herbicides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20150331 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: E. I. DU PONT DE NEMOURS AND COMPANY |
|
RAX | Requested extension states of the european patent have changed |
Extension state: ME Payment date: 20150413 |
|
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
INTG | Intention to grant announced |
Effective date: 20160606 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: ME |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: REF Ref document number: 847770 Country of ref document: AT Kind code of ref document: T Effective date: 20161215 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602013014511 Country of ref document: DE |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG4D |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: MP Effective date: 20161123 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 847770 Country of ref document: AT Kind code of ref document: T Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170224 Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170223 Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170323 Ref country code: ES Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602013014511 Country of ref document: DE |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SM Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: BE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: IT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170223 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 5 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed |
Effective date: 20170824 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20171031 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20171031 Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20171018 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E Free format text: REGISTERED BETWEEN 20180709 AND 20180711 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R082 Ref document number: 602013014511 Country of ref document: DE Representative=s name: MARKS & CLERK (LUXEMBOURG) LLP, LU Ref country code: DE Ref legal event code: R081 Ref document number: 602013014511 Country of ref document: DE Owner name: FMC CORPORATION (N.D.GES.D. STAATES DELAWARE),, US Free format text: FORMER OWNER: E.I. DU PONT DE NEMOURS AND COMPANY, INC., WILMINGTON, DEL., US |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20171018 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 6 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20171018 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: TP Owner name: FMC CORPORATION, US Effective date: 20181012 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: HU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO Effective date: 20131018 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CY Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: TR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161123 Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170323 |
|
P01 | Opt-out of the competence of the unified patent court (upc) registered |
Effective date: 20230503 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20231027 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20231025 Year of fee payment: 11 Ref country code: DE Payment date: 20231027 Year of fee payment: 11 |